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Friday July 10, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 6-July 10,2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 6th-July 10th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July 6th-July10th, 2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - July 10th CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - July10th SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - July 10th CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - July 10th SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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Saturday July 11, 2026
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Sunday July 12, 2026
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Monday July 13, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 13-July 17
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 13th-July 16th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 13th-July 17th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Flying Scot Simply Sail Private Lesson ( AH) Monday July 13th 100pm
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July13th-July 17th, 2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 13th - July 16th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Intermediate Flying Scot July 13th and July 15th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Tuesday July 14, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 13-July 17
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 13th-July 16th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 13th-July 17th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Catboat Simply Sail Private Lesson Tuesday July 14th at 1:00 (RL)
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July13th-July 17th, 2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 13th - July 16th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Wednesday July 15, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 13-July 17
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 13th-July 16th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 13th-July 17th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July13th-July 17th, 2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 13th - July 16th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Intermediate Flying Scot July 13th and July 15th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Thursday July 16, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 13-July 17
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 13th-July 16th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 13th-July 17th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Flying Scot Simply Sail Private Lesson ( AH) Thursday July 16th 100pm
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July13th-July 17th, 2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 13th - July 16th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Friday July 17, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 13-July 17
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 13th-July 17th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Flying Scot Simply Sail Private Lesson ( AH) Friday July 17h 100pm
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July13th-July 17th, 2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - July 17th SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - July17th CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - July 17th CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - July 17th SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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Sunday July 19, 2026
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Monday July 20, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 20-July 24
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 20th-July 23rd, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 20th-July 24th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July 20th-July 24th, 2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 20th - July 23rd
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Intermediate Flying Scot July 20th and July 22nd
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Tuesday July 21, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 20-July 24
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 20th-July 23rd, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 20th-July 24th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July 20th-July 24th, 2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 20th - July 23rd
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Wednesday July 22, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 20-July 24
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 20th-July 23rd, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 20th-July 24th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Flying Scot Simply Sail Private Lesson ( AH) Wednesday July 22nd 100pm
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July 20th-July 24th, 2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 20th - July 23rd
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Intermediate Flying Scot July 20th and July 22nd
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Thursday July 23, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 20-July 24
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 20th-July 23rd, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 20th-July 24th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Catboat Simply Sail Private Lesson Thursday July 23rd at 1:00pm (RL)
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July 20th-July 24th, 2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 20th - July 23rd
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Friday July 24, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 20-July 24
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 20th-July 24th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Flying Scot Simply Sail Private Lesson ( AH) July 24th Friday100pm
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July 20th-July 24th, 2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - July 24th CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - July24th SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - July 24th CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - July 24th SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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Saturday July 25, 2026
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Sunday July 26, 2026
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Monday July 27, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 27-July31,2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 27th-July 30th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 27th-July 31st, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Flying Scot Simply Sail Private Lesson ( AH) Monday July 27nd 100pm
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July 27th-July 31st,2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 27th - July 30th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Intermediate Flying Scot July 27th and July 29th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Tuesday July 28, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 27-July31,2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 27th-July 30th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 27th-July 31st, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Catboat Simply Sail Private Lesson Tuesday July 28th at 1:00pm ( RL)
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July 27th-July 31st,2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 27th - July 30th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Wednesday July 29, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 27-July31,2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 27th-July 30th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 27th-July 31st, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Flying Scot Simply Sail Private Lesson ( AH) Wednesday July 29th 100pm
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July 27th-July 31st,2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 27th - July 30th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Intermediate Flying Scot July 27th and July 29th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Thursday July 30, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 27-July31,2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing July 27th-July 30th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 27th-July 31st, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Flying Scot Simply Sail Private Lesson ( AH) Thursday July 30th 100pm
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July 27th-July 31st,2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scots July 27th - July 30th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Friday July 31, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots July 27-July31,2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail July 27th-July 31st, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Flying Scot Simply Sail Private Lesson ( AH) Friday July 31st 100pm
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Flying Scot Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Pleasant Bay Pass Holder Rentals - Afternoon Sunfish Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots July 27th-July 31st,2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - July 31st CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - July 31st SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - July 31st CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - July 31st SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:30 PM - 7:00 PM
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Pleasant Bay Pass Holder Rentals - Evening Catboat Rentals
Open to 2026 Pleasant Bay Pass Holders who have previously completed and passed a skills assessment with a member of PBCB's waterfront staff. To purchase a pass please click the link below.https://pbcb.cc/boat-kayak-rentals/pb-pass/To schedule a skills assessment in order to buy a pass, please call 508-945-7245 Monday through Friday from 9am to 3pm.
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Monday August 3, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots August 3-August 7, 2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing August 3rd-August 6th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail August 3rd-August 7th,2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots August 3rd-August 7th,2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scot August 3rd-August 6th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Intermediate Flying Scot August 3rd and August 5th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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Tuesday August 4, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots August 3-August 7, 2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing August 3rd-August 6th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail August 3rd-August 7th,2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots August 3rd-August 7th,2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scot August 3rd-August 6th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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Wednesday August 5, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots August 3-August 7, 2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing August 3rd-August 6th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail August 3rd-August 7th,2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots August 3rd-August 7th,2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scot August 3rd-August 6th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Intermediate Flying Scot August 3rd and August 5th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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Thursday August 6, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots August 3-August 7, 2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing August 3rd-August 6th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail August 3rd-August 7th,2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:00 PM
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"Simply Sail" Private Lessons - Catboat Simply Sail Private Lesson Thursday August 6that 1:00pm (RL)
Simply Sail: A private sailing experience
Offered from June through late August, is a two hour private sailing experience for up to 4 participants per boat/booking. Instruction is offered in your choice of a Catboat or Flying Scot and will be skippered by an experienced sailor. This is an opportunity to enjoy Pleasant Bay while getting an introduction to the basics of sailing–perfect for groups of friends or families!
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots August 3rd-August 7th,2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scot August 3rd-August 6th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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Friday August 7, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots August 3-August 7, 2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail August 3rd-August 7th,2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots August 3rd-August 7th,2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - August 7th CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly CATBOAT Races - August 7th SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - August 7th CREW
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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4:15 PM - 7:00 PM
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Friday Night Friendly FLYING SCOT Races - August 7th SKIPPER
Racing is a fun and challenging way to get more out of the sport of sailing. It provides an opportunity to reinforce and build your sailing skills while becoming part of a friendly community. Fine tune your boat handling skills through friendly competition. Skills checked sailors that have purchased a RACE PASS are welcome to skipper. If you wish to bring a crew that is also a skills checked sailor they as well need to have a RACE PASS, please have the sign up individually as "skills checked crew"Registration for each week will open the Monday prior to the race.You must sign up for each individual race you would like to participate in. Skills checked pass holders who want to crew and do not have a specified skipper are also welcome. Please also sign up as "skills checked crew". A Skipper's meeting will be held at 4:15 PM on the dock and all crew should be ready to go out by 4:30 PM. We will race until approximately 7 PM. Directly following the races, please join us on the bluff for a complimentary BBQ. PBCB will supply hamburgers, cheese, hot dogs, rolls, chips, paper products/cutlery, and condiments. Please feel free to bring your own beverages and/or a side to share. Post BBQ clean up will be a group effort.
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Monday August 10, 2026
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9:30 AM - 12:00 PM
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Beginner Youth Flying Scots / Ages 6-10 / Summer 2026 - Youth Flying Scots August 10-August 14, 2026
Open to ages 6 – 10 (older sailors, see Teen Flying Scots) Beginner to intermediate sailors will learn basic sailing skills on board a 19′ Flying Scot. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.Registration begins February 26th at 10:00am.Monday through Friday, 9:30 AM – noon $425/week Ages 6-10June 22-August 14, 2026
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9:30 AM - 3:00 PM
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Advanced All-Day Sailing for Teens & Tweens / Ages 10+ / Summer 2026 - Advanced All Day Sailing August 10th-August 13th, 2026
All-Day Sailing (for Teens and Tweens!)Monday through Thursday, 9:30 AM – 3 PM$675/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind.Students will sail Flying Scots in the mornings with a group of their peers and an instructor. As older and more experienced sailors, they will become comfortable sailing the boats as a team, practice making moorings, and may participate in some friendly races. In the afternoons, this group will join the Adventure Sailing group.We thoroughly enjoyed running this first-year program in 2025 and are excited to continue to offer this course! Students should bring a bagged lunch to enjoy with their peers and our staff from noon – 12:30 PM, between AM and PM sailing sessions.
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12:30 PM - 3:00 PM
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Advanced Youth Adventure Sail / Ages 10+ / Summer 2026 - Youth Adventure Sail August 10th-August 14th, 2026
Adventure SailingMonday through Friday, 12:30 – 3 PM$425/weekAges 10+Open to sailors ages 10+ who are independent skippers and fully confident with general rigging and skippering. Sailors should already be able to tack, jibe, avoid/get out of irons, and sail upwind. Students will fine tune their skills by exploring the bay or participating in friendly races. This class will most often use our Sunfish fleet, but instructors may also invite students to try 420 sailing, depending on wind conditions and student skill level.
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1:00 PM - 3:30 PM
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Teen Beginner Flying Scots / Ages 11-17 / Summer 2026 - Teen Flying Scots August 10th-August 14th,2026
Teen Flying ScotsMonday through Friday, 1 – 3:30 PM$425/weekAges 11+Beginners will learn the basics of sailing on board a Flying Scot sailboat. Students are assigned to small groups of similar age/experience level and sail with an instructor. This course aims to teach proper rigging/derigging, general water safety, tacking and jibing, and introduces the points of sail.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Beginner Flying Scot August 10th-August 13th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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4:30 PM - 7:00 PM
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Adult Flying Scot Sailing Lessons - Adult Intermediate Flying Scots August 10th & August 12th
The Flying Scot is a 19-foot centerboard sailboat designed for family sailing and racing. It’s known for being easy to sail, store, rig, and transport. The Flying Scot program focuses on developing sailing skills through a series of courses designed to help participants reach their sailing potential.Beginner Flying ScotsMonday through Thursday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$450/weekThis course if open to any person who has never sailed before, needs a refresher, or has sailed before but not in a Flying Scot. The course runs for four consecutive days and allows participants to experience varying weather conditions and instructor teaching styles while learning the basic sailing principles and skills. Many participants take this entry level course more than once before moving to the next level.Intermediate Flying ScotsMonday and Wednesday, 4:30 – 7 PMIf any weather-related cancellations occur during the week, your make up lesson will be offered on Friday evening. Please reserve the Friday evening of your course.$225/weekThis course expands on the basic building blocks from the Beginner class. The goal of this course is to gain confidence and independence, working towards becoming a solo skipper. This class is often repeated more than once by participants hoping to pass a skills check, which allows sailors to rent boats independently at PBCB.
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