Raise the sails or take the wheel on Martha's Vineyard waters
Water, soda water, cheese platter
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.
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
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.
Black Dog Wharf
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!!
Matthew Zent
August 17, 2026
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!!
Matthew Zent
August 17, 2026
Sail Martha's Vineyard aboard a historic 1926 schooner
Sail Vineyard Sound with lighthouse views and secluded swim options
Discover Martha’s Vineyard’s iconic cliffs and villages on a flexible private tour.
Tour an oyster farm by boat and enjoy freshly shucked oysters