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    Sail the Vineyard LLC

    Sail the Vineyard LLC

    4.9 • 32 reviews
    Tisbury, MA

    Sail the Vineyard invites guests to experience Martha’s Vineyard from the water aboard Phoenix, a sleek 44-foot classic sailboat. Led by Captain Wendy Lea, a US Coast Guard Master Mariner, certified sailing instructor, and accompl...

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    Book Sail the Vineyard LLC

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    Vineyard Haven Brunch Cruise

    Sail Vineyard Haven Harbor with brunch bites, mimosas, and live jazz

    $249.09
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    JAWS-Themed Sail on Martha's Vineyard

    Explore JAWS movie history with shark-themed drinks and trivia

    $216.60
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    Martha's Vineyard Sunset Sail

    Share an evening harbor sail as the light shifts over the water

    $216.60person
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    Private Sailing Charter in Martha's Vineyard

    Set sail on a private classic sloop tailored to your group

    From$731

    What people are saying

    Review 1 of 5
    5/5

    We celebrated my Mom’s 71st birthday with Captain Wendy and first “femate” Cassie and it was an amazing experience. They took care of everything and it was such a relaxing sail. Highly recommend for those who want to be out on a safe sailboat and celebrate with some drinks, snacks, laughs and fun.

    Photo of peschke66

    peschke66

    August 14, 2026

    Review 1 of 1
    5/5

    We celebrated my Mom’s 71st birthday with Captain Wendy and first “femate” Cassie and it was an amazing experience. They took care of everything and it was such a relaxing sail. Highly recommend for those who want to be out on a safe sailboat and celebrate with some drinks, snacks, laughs and fun.

    Photo of peschke66

    peschke66

    August 14, 2026