Sailing Excursion Options
2-Hour Harbor Sails
Sunsets & Special Occasions
3- or 4-Hour Day Sails
Experience the beauty of Martha's Vineyard island on one of our sailing charters, either a day sail or a sunset sail, and 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 charters may be scheduled
any time of day.
2 Hour Charters
Private, Up to 6 People
$625
In compliance with U.S. Coast Guard CFR Subchapter C, we carry a maximum of 6 guests, but have options for larger groups.
Call for details.
Requests are considered, however, for your safety and enjoyment, the Captain will determine the best route for your sail based on current, tide, and wind conditions on the day and time of your sail.
3- or 4-Hour Day Sails
Sunsets & Special Occasions
3- or 4-Hour Day Sails
Venture outside the Vineyard Haven 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.
3 Hour Charters
Private, Up to 6 People
$775
4 Hour Charters
Private, Up to 6 People
$900
In compliance with U.S. Coast Guard CFR Subchapter C, we carry a maximum of 6 guests, but have options for larger groups.
Call for details.
Requests are considered, however, for your safety and enjoyment, the Captain will determine the best route based on tide, current and wind conditions on the day and time of your sail.
Sunsets & Special Occasions
Sunsets & Special Occasions
Sunsets & Special Occasions
Make a toast to another perfect day in paradise with a sunset sail around the harbor. Sunsets are always special on Martha's Vineyard, but from the water aboard a sailing vessel they take on a magical quality. Celebrating a birthday, anniversary or proposal? Sunset sails are the perfect venue for your special evening.
2 Hour Charters
Private, Up to 6 people
$650
Traveling solo or want the camaraderie of fellow travelers? Click here to visit our
In compliance with U.S. Coast Guard CFR Subchapter C, we carry a maximum of 6 guests, but have options for larger groups.
Call for details.
Requests are considered, however, for your safety and enjoyment, the Captain will determine the best route based on tide, current and wind conditions on the day and time of your sail.
Sailing charters from Vineyard Haven including day sailing & sunset sails.
Limited to just 6 guests, these small group sunset sails are perfect for solo travelers and couples who prefer the camaraderie of others over a private sail!
Add On Catering Options
Gourmet Hors d'oeuvre Platters
Gourmet Hors d'oeuvre Platters
Gourmet Hors d'oeuvre Platters
Leave the snacks to us!
Not only do we include soda & snacks on all our charters, we offer delicious platters with a variety of cheeses, fruits, charcuterie and crackers. They're complimentary on our 4-hour sails, but you can add them on shorter sails. Interested in something more filling? Ask about our other catering options.
$100
Dessert Platters
Gourmet Hors d'oeuvre Platters
Gourmet Hors d'oeuvre Platters
Everyone knows salty & sweet go together perfectly!
If the salt air gives you a sweet tooth, we've got you covered. Add a gourmet dessert platter with a variety of local fudge, cookies, and other sweets to any sail.
$100
Countdown to Summer!
Punxsutawney Phil may have predicted 6 more weeks of winter, but it's the perfect time to plan your summer sail!
Please note our new phone number:
508.493.8767