Charters from US $525

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Great Evening on the Water

VERIFIED NEW 4 Hour Sunset Charter on June 21, 2026

Todd R.

5.0 / 5

Great Evening on the Water

VERIFIED NEW

Todd R.

5.0 / 5

Experience:

5.0 / 5

Boat

5.0 / 5

Crew

5.0 / 5

Overall

From the start, Jonathan was both a gracious host and a skilled, knowledgeable captain. His communication with us both before and during our 4-hour sunset cruise was casual, welcoming and thorough- and helped us enjoy every step along the way. “Windswept” was comfortable, capable and beautifully maintained- making for a relaxing, yet engaging sailing experience. Highly recommend!

From the start, Jonathan was both a gracious host and a skilled, knowledgeable captain. His communication with us both before...

Todd R. recommends Windward Sailing Charters

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1 person finds this review helpful

Reviews by other customers

Rating summary

5.0 / 5

out of 5 stars from 3 reviews

See details

Boat

5.0 / 5

Crew

5.0 / 5

Experience

5.0 / 5

Photos & videos by reviewers (3)

Customer rating

5 stars		3
4 stars		0
3 stars		0
2 stars		0
1 star		0

Customers claimed

Good experience
	100%
Friendly captain
	100%
Recommend this charter
	100%
Appropriate for children
	67%
Satisfied with the boat
	100%

Appropriate for children
	67%
Satisfied with the boat
	100%

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Showing:

3 of 3 reviews

Showing 1 - 3 of 3 reviews

Amanda J.

5.0 / 5

Experience:

5.0 / 5

Boat

5.0 / 5

Crew

5.0 / 5

Overall

Amazing!

VERIFIED 3 Hour Private Sailing Charter on August 2, 2025

Amanda J.

5.0 / 5

Aug 2, 2025

3 Hour Private Sailing Charter

Amazing!

VERIFIED

Jonathon welcomed my friends & I aboard as if we were family! He went above & beyond to make us comfortable in his space. He was very knowledgeable in sailing as my husband loves to learn & chat about it all. The boat was the perfect size for the 5 of us with plenty of room. The bathroom was so large for a sail boat! Getting to the sailboat was so easy & quick. We will definitely be looking to book with Jonathon again.

Jonathon welcomed my friends & I aboard as if we were family! He went above & beyond to make us comfortable in his space. He...

Amanda J. recommends Windward Sailing Charters

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Jonathan Puleio (The Captain)

Replied on August 4, 2025

Thanks so much for taking the time to write a review! I’m so happy to hear that everyone had a great experience! Hope to see everyone again one day!

Jonathan Puleio (The Captain)

Replied on August 4, 2025

Thanks so much for taking the time to write a review! I’m so happy to hear that everyone had a great experience! Hope to see everyone again one day!

Captain replied

Crystal F.

5.0 / 5

Experience:

5.0 / 5

Boat

5.0 / 5

Crew

5.0 / 5

Overall

Best trip

VERIFIED NEW 3 Hour Private Sailing Charter on June 21, 2026

Crystal F.

5.0 / 5

Jun 21, 2026

3 Hour Private Sailing Charter

Best trip

VERIFIED NEW

highly recommend this experience with Johnathon

Crystal F. recommends Windward Sailing Charters

Mark review as helpful

Crystal F. recommends Windward Sailing Charters

Mark review as helpful

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Great Evening on the Water

Great Evening on the Water

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Amazing!

Amazing!

Best trip

Best trip

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Great Evening on the Water

Great Evening on the Water

Reviews by other customers

Amazing!

Amazing!

Best trip

Best trip

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