Ranked #1 on TripAdvisor 2018, 2019, 2020 & 2021
Looking for a slightly smaller, budget friendly option?
Sail The Vineyard aboard our sister ship, M/S Resolute
The thrill of this sleek, fast Classic Islander sloop-rigged sailboat is the perfect adventure for your vacation to the Martha's Vineyard. Feel the thrill of the wind in your hair or find your inner pirate and help us raise the sails, grind the winches and hoist the colors - arrrr!
508.923.7177
Day Sails Aboard Our Sister Ship
2-hour day sail
$500
Experience the beauty of Martha's Vineyard island as you explore the inner harbor of Vineyard Haven. Relax and bask in the sun or take a more active role and help with the activities of sailing.
2-hour sunset sail
$500
Sunsets are always special on Martha's Vineyard, but when enjoyed from the water aboard a sailing vessel they take on a magical quality. Make a toast to another perfect day in paradise with a sunset sail around the inner harbor. Celebrating a birthday, anniversary or proposal? Sunset sails are the perfect venue for your special evening. These sailing depart Vineyard Haven Harbor.
4-hour day sail
$750
Venture outside the Vineyard Haven inner harbor with us and enjoy sailing more of the Martha's Vineyard coastline. Bring your own prepared foods, utensils & alcoholic beverages, or ask about catering for a picnic underway.
508.923.7177
New Options for Groups Larger Than 6!
Check out The Vineyard's Newest, Exclusive Sailing Option