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Tuesday September 1, 2026
2:00 PM - 4:00 PM    "Simply Sail" Private Lessons - Simply Sail with Louise - Tuesday September 1st - 2 - 4 PM
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Flying Scot Rentals
 
Wednesday September 2, 2026
2:00 PM - 4:00 PM    "Simply Sail" Private Lessons - Simply Sail with Joy - Wednesday September 2nd - 2 - 4 PM
 
2:00 PM - 4:00 PM    "Simply Sail" Private Lessons - Simply Sail with Louise - Wednesday September 2nd - 2 - 4 PM
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Flying Scot Rentals
 
Thursday September 3, 2026
2:00 PM - 4:00 PM    "Simply Sail" Private Lessons - Simply Sail with Louise - Thursday September 3rd - 2 - 4 PM
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Flying Scot Rentals
 
Friday September 4, 2026
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Flying Scot Rentals
 
Saturday September 5, 2026
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Flying Scot Rentals
 
Sunday September 6, 2026
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 8/31 - 9/6: Afternoon Flying Scot Rentals
 
Tuesday September 8, 2026
9:00 AM - 12:00 PM    2026 Catboat Cruises - Catboat Cruise Tuesday Sept 8th 9am -12pm CREW
 
9:00 AM - 12:00 PM    2026 Catboat Cruises - Catboat Cruise Tuesday Sept 8th 9am -12pm SKIPPER
 
2:00 PM - 4:00 PM    "Simply Sail" Private Lessons - Simply Sail with Louise - Tuesday September 8th - 2 - 4 PM
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/8 - 9/11: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/8 - 9/11: Afternoon Flying Scot Rentals
 
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Wednesday September 9, 2026
9:00 AM - 12:00 PM    2026 Catboat Cruises - Catboat Cruise Wednesday Sept 9th 9am -12pm CREW
 
9:00 AM - 12:00 PM    2026 Catboat Cruises - Catboat Cruise Wednesday Sept 9th 9am -12pm SKIPPER
 
2:00 PM - 4:00 PM    "Simply Sail" Private Lessons - Simply Sail with Joy - Wednesday September 9th - 2 - 4 PM
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/8 - 9/11: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/8 - 9/11: Afternoon Flying Scot Rentals
 
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Thursday September 10, 2026
2:00 PM - 4:00 PM    "Simply Sail" Private Lessons - Simply Sail with Charlie - Thursday September 10th - 2 - 4 PM
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/8 - 9/11: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/8 - 9/11: Afternoon Flying Scot Rentals
 
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Friday September 11, 2026
2:00 PM - 4:00 PM    "Simply Sail" Private Lessons - Simply Sail with Charlie - Friday September 11th - 2 - 4 PM
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/8 - 9/11: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/8 - 9/11: Afternoon Flying Scot Rentals
 
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Saturday September 12, 2026
9:00 AM - 2:00 PM    Sandpiper Invitational - Sandpiper Invitational Racers - Bring Your Own Boat (non-PBCB boats)
 
9:00 AM - 2:00 PM    Sandpiper Invitational - Sandpiper Invitational Racers - PBCB Boats
 
4:00 PM - 8:00 PM    Sandpiper Invitational - Sandpiper Invitational After Party/Dinner - Saturday September 12th at 4 PM
 
Sunday September 13, 2026
10:30 AM - 1:30 PM    Sandpiper Invitational - Sandpiper Invitational Sunday Morning Cruise September 13th 10am PBCB Boat CREW
 
10:30 AM - 1:30 PM    Sandpiper Invitational - Sandpiper Invitational Sunday Morning Cruise September 13th 10am PBCB Boat SKIPPER
 
Monday September 14, 2026
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Flying Scot Rentals
 
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
3:30 PM - 4:30 PM    Rewilding Sipson Island - a Native Plant Walk & Solar-powered Pontoon Boat Ride - Plant Walk and Talk on Sipson Island - Monday Sept 14th - 3:30 - 5:30 PM (Cpt Bart/Mate Miranda)
 
Tuesday September 15, 2026
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Flying Scot Rentals
 
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Wednesday September 16, 2026
2:00 PM - 4:00 PM    "Simply Sail" Private Lessons - Simply Sail with Joy - Wednesday September 16th - 2 - 4 PM
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Flying Scot Rentals
 
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Thursday September 17, 2026
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Flying Scot Rentals
 
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Friday September 18, 2026
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Catboat Rentals
 
2:00 PM - 5:00 PM    Pleasant Bay Pass Holder Rentals - 9/14 - 9/18: Afternoon Flying Scot Rentals
 
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Saturday September 19, 2026
9:30 AM - 10:30 AM    Celebrate our Waters on Pleasant Bay - Celebrate our Waters Sailing - Saturday September 19th at 9:30am
 
10:30 AM - 11:30 AM    Celebrate our Waters on Pleasant Bay - Celebrate our Waters Sailing - Saturday September 19th at 10:30am
 
12:00 PM - 1:00 PM    Celebrate our Waters on Pleasant Bay - Celebrate our Waters Sailing - Saturday September 19th at 1200pm
 
Monday September 21, 2026
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Tuesday September 22, 2026
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Wednesday September 23, 2026
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
3:00 PM - 6:00 PM    Float and Paint aboard our Floating Classroom - Float & Paint Wednesday September 23rd 3:00pm Capt. Bart/ Mate JP
 
Thursday September 24, 2026
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
4:30 PM - 5:30 PM    Bog Walk & Talk: September 24th at 4:30 PM - Bog Walk & Talk: September 24th at 4:30 PM
 
Friday September 25, 2026
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Monday September 28, 2026
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Tuesday September 29, 2026
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Wednesday September 30, 2026
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers
 
Thursday October 1, 2026
3:00 PM - 5:30 PM    Pleasant Bay Explorers (Ages 7-14) - Pleasant Bay Explorers