Tandemeer Sailing Tour: Vineyard Haven Exploration
5 Ratings

For a unique perspective of Vineyard Haven Harbor, Nantucket Sound, and Vineyard Sound, sailing is unparalleled. Board the Tandemeer, a 60-foot ketch from 1980, acclaimed for its appearance in the 1982 blockbuster ‘Trading Places’ featuring Eddie Murphy, Dan Akroyd, and Jamie Lee Curtis. Enjoy sun-drenched fun with a touch of elegance.

Duration: 2 hours
Cancellation: 1 day learn more
  • Vineyard Haven - Sailing on beautiful classic 60 foot ketch sailboat Tandemeer, out from Vineyard Haven Harbor into Nantucket Sound and Vineyard Sound, enjoying the sun, wind, water and views of the Cape, Islands and other boats.
  • West Chop Lighthouse - We will sail by and enjoy a nice view of the West Chop Lighthouse from the water.
  • East Chop Lighthouse - We will sail by and enjoy a nice view of the East Chop Lighthouse from the water.
What's Included
  • Carbonated beverages
  • Bottled water
  • Snacks
What's Not Included
  • Guests are welcome to BYO alcohol beverages for those over 21.
  • Dinner
  • Lunch
Additional Information
  • No Children under 5, kids under 14 must wear life jackets.
Black Dog Wharf
Beach Street
Walk out on the Black Dog Wharf to the Vineyard Haven Launch dock, get on the Launch, ask the driver to take you out to Tandemeer. Pay the Launch driver $4 per person.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
(5 Ratings)
5 stars
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1 star
Aug 21, 2023
Private, lovely, fun and very reasonable. - It was our anniversary, and we wanted to do something special without totally breaking the bank and without a bunch of other people. This was lovely, our own private sail on a big old romantic sailboat. The captain and crew member were perfect, chatting with us when we wanted to be chatting, and leaving us on our own otherwise. We booked a 2 hour cruise for the sunset with plans to go out to dinner afterwards, but when we found out there were fireworks we were able to extend our sail to watch them. The captain did a fantastic job of maneuvering so that we had a wonderful view while we lounged on big comfortable bean bag chairs. The crew member brought us beautiful charcuterie boards and flat breads and kept our wine glasses full. The boat was easy to get on and off of and the little launch that brought us back and forth was pleasant. If you want a private "get away" I can't recommend these folks enough.
Review provided by Tripadvisor
Aug 12, 2023
1st Martha's Vineyard trip 2023 - The beautiful sunset, to the friendly, informative and warm Captain and crew, made our experience memorable!
Review provided by Viator
Aug 5, 2023
Absolutely Devine!!! - Great Captain, lovely sailing!! ☺️👍💃Excellent, friendly service and an all around great time; we hardly recommend Island Sailing Tours
Review provided by Viator
Jul 13, 2022
extremely professional, attentive, and friendly - Captain and crew are extremely professional, attentive, and friendly. The cooking and hospitality are top class. At 60 feet, Tandemeer is one of the largest sailboats I have been on.
Review provided by Tripadvisor
Aug 13, 2023
TripAdvisor Terrible - Trip was fantastic. Interaction with TripAdvisor was terrible. TripAdvisor did not coordinate with vendor. I booked with TripAdvisor on one date but told by vendor, it was not availble. Changed booking but word never got to TripAdvisor even though I tried contacting them. They billed me on the original date and deluged me with spam email. WTF.
Review provided by Tripadvisor
Select Date and Tickets
up to 6 guests
May 2024