Sail The Vineyard
Sail The Vineyard
5
Boat Tours • Sightseeing Tours • Private Tours • Day Trips
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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, fast, classic sailboat with Master Mariner & 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 M.S. Resolute with us!
Vineyard Haven, Massachusetts

Awards
Travellers' Choice
2022

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(65 reviews)
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Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
Popular mentions

5.0
90 reviews
Excellent
89
Very good
1
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Terrible
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Julia W
Lima, Peru26 contributions
Sep. 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.

Patty
3 contributions
Sep. 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.

Scott S
1 contribution
Sep. 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.

jamestV3232VD
Denver, CO2 contributions
Sep. 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.

Mcs1025
Monroe, NJ12 contributions
Sep. 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.

plm124
New Jersey15 contributions
Sep. 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.

jaykay50
Chicago, IL7 contributions
Sep. 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.

Lindsay M
1 contribution
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.

Yasemin W
Washington DC, DC3 contributions
Aug. 2022
We had an excellent sail with Captain Wendy! I was overwhelmed by the various groups/charters offering sails on the Vineyard. Tripadvisor reviews, a call answered in real time by her, and the added bonus of supporting a female owned business landed us with Captain Wendy. She, her crew and her boat are all amazing! Our family of 5 was celebrating my husband's 50th birthday and the Sail The Vineyard team made sure it was extra special. We've been summer visitors for decades yet had never done a private sail. Perfect way to see Vineyard Haven Harbor - East Chop, West Chop and more! Captain Wendy had stories to share and even answered our random questions. We chose the 2 hour sail not knowing how we'd fare. Now we know to do longer. Can't wait to go again next season!
Highly recommend Sail the Vineyard for a safe, personable, and extraordinary outing. No need to stress over the options - choose Captain Wendy!
Written August 29, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Mykiyaa s
1 contribution
Aug. 2022 • Couples
Had an amazing time with family and friends. Can’t wait to come back for another sailing experience!
Written August 21, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

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SAIL THE VINEYARD (Vineyard Haven) - 2023 What to Know BEFORE You Go