"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 Monday June 22nd at 1pm 
18y and up N/A M  06/22/2026
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 Tuesday June 23rd at 100pm 
18y and up N/A Tu  06/23/2026
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 Wednesday June 24th at 100pm 
18y and up N/A W  06/24/2026
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 Friday June 26th at 100pm 
18y and up N/A F  06/26/2026
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 June 30th 1:00PM 
18y and up N/A Tu  06/30/2026
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 July 9th at 1:00PM 
18y and up N/A Th  07/09/2026
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 July 14th at 1:00 
18y and up N/A Tu  07/14/2026
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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Catboat Simply Sail Private Lesson Thursday July 23rd at 1:00pm 
18y and up N/A Th  07/23/2026
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 July 28th at 1:00pm 
18y and up N/A Tu  07/28/2026
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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Catboat Simply Sail Private Lesson Thursday August 6that 1:00pm 
18y and up N/A Th  08/06/2026
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 
18y and up N/A Tu  08/11/2026
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 Thursday August 20th at 1:00pm 
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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Catboat Simply Sail Private Lesson Tuesday August 25th at 1:00pm 
18y and up N/A Tu  08/25/2026
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
* Adjustments and discounts will be applied during checkout if applicable. *

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