Martha's Vineyard Things To Do: Sailing Excursions

Join us at Sail The Vineyard for an unparalleled sailing experience along the stunning coastline of Martha's Vineyard island in Massachusetts. A Martha's Vineyard boat charter is truly one of the best things to do in Martha’s Vineyard and the best way to the see the area. Below are some of our top sail MV excursions.

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Chose one of these curated boat trips, or call us to create your own. These Martha's Vineyard boat rentals all include a Captain and Crew for your safety and enjoyment.

Martha's Vineyard Island Day Sails (public or private)

Martha's Vineyard Island Sunset Sails (public or private)

4th of July Fireworks Sails

Grand Illumination Fireworks Sails

Weddings & Vow Renewals

JAWS Martha's Vineyard 50th Anniversary Sail

Under The Sea Kids Sails

Sips & Sails: A Jazzy Brunch Cruise

Liveaboard Vacation Sails

Sailing Instruction

And don't forget that everything tastes better on a boat! We offer everything from gourmet hors d'oeuvres to desserts to scrumptious sandwich platters! See below for options or contact us to make a special request.

Experience the Thrill of Sailing with the best of Martha's Vineyard Island

Welcome to Sail The Vineyard, where sailing isn't just our job, it's our passion! We’re consistently ranked as a top Martha's Vineyard boat chartertour company on travel sites because our love for what we do shines from the moment you step aboard. We offer a wide range of sailing experiences to suit every taste – whether you’re a beached mermaid or escaped pirate; beginner or hard core sailor. Although it's quite rare to find a true ability to rent a boat on Martha's Vineyard, our experienced Captains and Crew are passionate about sailing and dedicated to providing you with a memorable Martha's Vineyard sailing charter trip, which affords you the ability to relax and watch the coastline go by.

Our guests visit us not only on Martha's Vineyard island for sailing tours but also in stellar sailing vacation destinations like the Caribbean - including stunning locations such as the Virgin Islands, The Grenadines, or St. Martin, to name a few - or far away dream destinations like Tahiti, Bora Bora, Thailand or The Whitsunday Islands of Australia. Wherever your sailing bucket list leads you, we can help you embrace the sailing lifestyle there.

Don't see what you have in mind? Contact us and we can design the perfect Martha's Vineyard boat charter trip just for you!

Browse our website to learn more and book your next sailing adventure today!

Your Safety & Where We Go

Safety

We always aim for giving our guests the sailing trip of a lifetime. To us, that means not only a fun day on the water, but a safe sailing excursion. The U.S. Coast Guard has established safety guidelines in CFR Subchapter C, that allow a maximum of 6 guests for any boat that doesn't have a special "inspected vessel" designation. Sure, there are some companies who bend that rule, but we believe keeping you safe is more important that anything else we do. If you have a group larger than 6, please contact us for details about how we can accommodate larger groups.
Where we go

Each of our sails is different because we work in a weather-dependent environment with winds, tides and currents that are always on the move! The descriptions of our sailing excursions provide some information about our typical itineraries. 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.