"Simply Sail" Private Lessons

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!
Register Activity Ages Grades Days Date/Time Fees
 
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Flying Scot Simply Sail Private Lesson ( AH) Wednesday August 12th 100pm 
18y and up N/A W  08/12/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
1 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Flying Scot Simply Sail Private Lesson ( AH) Thursday August 13th 100pm 
18y and up N/A Th  08/13/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
0 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Flying Scot Simply Sail Private Lesson ( AH) Friday August 14th 100pm 
18y and up N/A F  08/14/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
0 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Flying Scot Simply Sail Private Lesson ( AH) Monday August 17th 100pm 
18y and up N/A M  08/17/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
1 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Flying Scot Simply Sail Private Lesson ( AH) Wednesday August 19th 100pm 
18y and up N/A W  08/19/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
0 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Flying Scot Simply Sail Private Lesson ( AH) Thursday August 20th 100pm 
18y and up N/A Th  08/20/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
1 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Flying Scot Simply Sail Private Lesson ( AH) Friday August 21th 100pm 
18y and up N/A F  08/21/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
0 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Flying Scot Simply Sail Private Lesson ( AH) Monday August 24th 100pm 
18y and up N/A M  08/24/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
0 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Flying Scot Simply Sail Private Lesson ( AH) Wednesday August 26th 100pm 
18y and up N/A W  08/26/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
0 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Flying Scot Simply Sail Private Lesson ( AH) Friday August 28th 100pm 
18y and up N/A F  08/28/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
1 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Flying Scot Simply Sail Private Lesson ( AH) Monday August 31st 100pm 
18y and up N/A M  08/31/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
1 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Catboat Simply Sail Private Lesson Tuesday August 11th at 1:00pm (RL) 
18y and up N/A Tu  08/11/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
0 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Catboat Simply Sail Private Lesson Thursday August 20th at 1:00pm ( RL) 
18y and up N/A Th  08/20/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
0 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
 
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Catboat Simply Sail Private Lesson Tuesday August 25th at 1:00pm ( RL) 
18y and up N/A Tu  08/25/2026
01:00 PM - 03:00 PM
Boat House Beach 		$250.00 YR, $250.00 SR
0 seat(s) available
a two hour private sailing experience for up to 4 participants per boat/booking
* Adjustments and discounts will be applied during checkout if applicable. *

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