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    1. Local experiences
    2. /Things to do in Vineyard Haven…
    3. /Water Activities
    4. /Sailing
    5. /Martha's Vineyard Historic Schooner Sailing Cruise
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    Martha's Vineyard Historic Schooner Sailing Cruise

    Raise the sails or take the wheel on Martha's Vineyard waters

    4.8 stars• 86 reviews

    Includes

    Water, soda water, cheese platter

    Highlights

    Explore Martha's Vineyard aboard the Schooner Alabama, built in 1926. Join the crew, take the wheel with the captain, or relax and enjoy the scenery.

    • Help raise the sails with the crew
    • Take a turn at the wheel with the captain
    • Enjoy an afternoon or evening sail
    • Bring your own drinks and picnic meal

    What's Included

    • Water
    • Soda water
    • Cheese platter

    Important details

    • Arrive 20 minutes early
    • Dress appropriately for the weather
    • Requires climbing a short ladder to board and depart the water taxi
    • Requires using a stairwell-style ladder to access below-deck cabins and bathrooms

    Cancellation Policy

    Receive a full refund when you cancel or reschedule more than 48 hours before the sail. No-shows are charged the full price. Receive a full refund if the operator cancels due to weather or unforeseen circumstances.

    Product ID: 589SF9

    FAQs

    The historic schooner is not handicap accessible. Boarding and departing require climbing a short ladder from the water taxi, and accessing below-deck cabins and bathrooms requires using a stairwell-style ladder.

    Meeting details

    Black Dog Wharf

    Experience provided by Black Dog Tall Ships

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Adult

    $107

    Ages 13+

    0

    Child

    $64.20

    Ages 4-12

    0

    Infant

    $0

    Ages 3 and Under

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    What people are saying

    Review 1 of 5
    5/5

    The sunset sail was an amazing way to kick off our family vacation week on Martha's Vineyard! This was our third sail on the Alabama, and while all have been fantastic this one was extra special. My daughters and niece had a great time sailing under the guidance of the wonderful Captain Jamie while the family enjoyed a peaceful sail with incredible views. Both captain and crew were welcoming, accommodating and incredibly knowledgeable. If you're looking for an authentic experience and a chance to step back into the past and experience what it was like to sail these beautiful waters 100 years ago, the Alabama is a can't miss!! Thank you for the memories!!

    Photo of Matthew Zent

    Matthew Zent

    August 17, 2026

    Review 1 of 1
    5/5

    The sunset sail was an amazing way to kick off our family vacation week on Martha's Vineyard! This was our third sail on the Alabama, and while all have been fantastic this one was extra special. My daughters and niece had a great time sailing under the guidance of the wonderful Captain Jamie while the family enjoyed a peaceful sail with incredible views. Both captain and crew were welcoming, accommodating and incredibly knowledgeable. If you're looking for an authentic experience and a chance to step back into the past and experience what it was like to sail these beautiful waters 100 years ago, the Alabama is a can't miss!! Thank you for the memories!!

    Photo of Matthew Zent

    Matthew Zent

    August 17, 2026

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