Sail The Vineyard
Sail The Vineyard
5
Boat ToursSightseeing ToursPrivate ToursDay Trips
10:00 AM - 8:00 PM
Monday
10:00 AM - 8:00 PM
Tuesday
10:00 AM - 8:00 PM
Wednesday
10:00 AM - 8:00 PM
Thursday
10:00 AM - 8:00 PM
Friday
10:00 AM - 8:00 PM
Saturday
10:00 AM - 8:00 PM
Sunday
10:00 AM - 8:00 PM
About
Experience Martha's Vineyard sailing aboard our sleek, classic sailboat with our USCG Master Mariner, RYA Yachtmaster Offshore & ASA-Certified Sailing Instructor, Captain Wendy. Exploring the beauty & history of the area by sea is the perfect adventure for your Vineyard vacation. The picturesque coastline of lighthouses, historic homes, and beautiful beaches are just a few of the beloved sights of the area. Sail aboard Phoenix with us!
Vineyard Haven, Massachusetts

Awards
Travellers' Choice
2023

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Travellers talk about
(65 reviews)
(2 reviews)
(4 reviews)

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as waiting time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles92 reviews
Excellent
91
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1
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0
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0
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Trek813875
Monclova, OH5 contributions
5.0 of 5 bubbles
Sept 2023 • Couples
Captain Wendy and crew are fun and engaging. Great knowledge of the area. Beautiful boat. Exactly what we’d hoped it would be.
Written September 3, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Dawn B
New York City, NY8 contributions
5.0 of 5 bubbles
Aug 2023 • Family
This was our second trip with Captain Wendy and it was even better than the last! The crew is so friendly, the views are spectacular and the music and vibes were amazing!
We will continue to come back every year!
Written August 29, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Julia W
Fenton, MI29 contributions
5.0 of 5 bubbles
Sept 2022
Captain Wendy was a delight. She was very friendly and willing to share her love of sailing with our group. We enjoyed our sunset cruise very much.
Written September 20, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Patty
3 contributions
5.0 of 5 bubbles
Sept 2022
Great sunset cruise with an excellent captain! Captain Wendy is experienced, professional and friendly (plays great music) and provided us with an amazing sailing cruise! Would definitely join her again!
Written September 20, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Scott S
1 contribution
5.0 of 5 bubbles
Sept 2022 • Family
The last 10 minutes as we coasted in as the sun set over the harbor we’re magnificent. Wendy handled our group as a kind professional, knowing when to allow us some space and when to engage us. She let our 84 yo mother take the wheel and allowed us to raise the sails. She is so pleasant and accommodating.
Written September 16, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

jamestV3232VD
Denver, CO3 contributions
5.0 of 5 bubbles
Sept 2022
We sailed right out of Vineyard Harbor and caught a wonderful fresh wind. Sailed down towards Edgartown with lots of sights and landmarks along the way. Captain Wendy was most accommodating . She is so knowledgeable and handled the boat like it was nothing. We brought wine with us, so asked to sail a little more level and she kept us all dry. I would highly recommend sailing with her.
Written September 16, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Mcs1025
Monroe, NJ14 contributions
5.0 of 5 bubbles
Sept 2022 • Family
Thanks Captain Wendy for a great charter for me and my family this past week. We ended up with the perfect day on the perfect sailboat with the perfect captain ! You're the best! Thanks for making this first time sailing experience for my nieces memorable and fun ! See you next time ! Cheers ! Michele
Written September 11, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

plm124
New Jersey15 contributions
5.0 of 5 bubbles
Sept 2022 • Family
What a glorious way to spend our last day at Martha’s Vineyard! Captain Wendy took our family on a beautiful and relaxing 2-hour sail around the the island and although our two young grandchildren were a bit hesitant at first, by the time we returned to dock, they were ready to set sail again! Wendy was the greatest - we felt safe and in good hands - like sailing with a good friend! I highly and strongly recommend you set sail aboard Captain Wendy’s lovely ship - I plan on a longer sail on my next trip!
Written September 11, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

jaykay50
Chicago, IL7 contributions
5.0 of 5 bubbles
Sept 2022 • Friends
Captain Wendy was great! Provided us with good information as we sailed to see a beautiful sunset. Very chill environment - perfect way to wrap up a great day.
Written September 4, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Lindsay M
1 contribution
5.0 of 5 bubbles
Jul 2022 • Friends
My girlfriends and I went to Martha’s Vineyard for our 45th birthday celebration and enjoyed the sail the vineyard excursion so much! Our captain and co-captain was an all female team and they were amazing! It’s a definite must if you are in the area.
Written August 30, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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Sail The Vineyard - All You Need to Know BEFORE You Go (2024)

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