Private Day Sail and Sunset Sail Options
Vineyard Haven Harbor Sails: 2-Hour Sails
Martha's Vineyard Day Sails: 3 or More Hours
Martha's Vineyard Day Sails: 3 or More Hours
Experience the beauty of Martha's Vineyard island on one of our sailing charters and explore the inner harbor of Vineyard Haven.
Our expansive harbor is a sailor's playground. Generally well-protected and calm, this harbor tour is a fantastic way for "first-timers" to sail Martha’s Vineyard. Plus it’s a fantastic opportunity to enjoy just enough of an escape from the crowds of land life. Learn about the history of the island and Vineyard Haven with a quick circle through the inner harbor if you like. Relax and bask in the sun or take a more active role and help with the activities of sailing. Offered daily, this is our most popular sail.
2-hour charters may be scheduled
any time of day.
2 Hour Charters
Private, Up to 6 People
$675
Our sunset sail is also typically a 2-hour sail. Visit our sunset sail page for details.
Don't forget the ship's rations! We can cater your sail with gourmet hors d'oeuvre or dessert platters as purchase add-ons for our 2-hour sails. You'll be able to add them to your cart during the reservations process.
Martha's Vineyard Day Sails: 3 or More Hours
Martha's Vineyard Day Sails: 3 or More Hours
Martha's Vineyard Day Sails: 3 or More Hours
Sometimes you just need a happy medium! For those who feel like a 2-hour Martha's Vineyard sailing charter is too short but 4 just might be too much for unseasoned sea legs, our 3-hour sailing trip takes us beyond the harbor. Venture out into Vineyard Sound with us and enjoy sailing a little more of the Martha's Vineyard island coastline.
3 Hour Sailing Charters
Private, Up to 6 People
$825
If you just live to be on the water like we do, a 2-3 hour Martha's Vineyard boat charter just isn't enough! Hoist the sails with us and let's set sail for far away shores - or at least one outside the harbor. With 4 hours we can sail Martha’s Vineyard Sound; a bit longer and we can make a full day destination sail to the Elizabeth Islands, Lambert’s Cove, Menemsha or other exciting locations.
4 Hour Sailing Charters
Private, Up to 6 People
$1100
We offer longer trips and full-day excursions. Call for details and pricing.
Don't forget the ship's rations! Gourmet hors d'oeuvre or dessert platters are just the beginning. Let us pamper you with a fabulous sandwich platter or cater a full picnic aboard. Call for pricing and details.
*Hors d’oeuvre platters are included on sails of 4+ hours and can be added to your cart for any sail of 2-4 hours..
Martha’s Vineyard Sunset Sails & Special Occasions
Watch one of nature’s most glorious scenes as the sun dips below the horizon, painting the sky in breathtaking colors. Our Martha's Vineyard sunset sails are intentionally calm and relaxed, offering the perfect way to sail Martha’s Vineyard at the most beautiful hour of the day.
Step aboard and slow down, sip a glass of wine, and enjoy the quiet magic as the harbor glows in the evening light. Whether you choose a private or public sunset sail, a Martha’s Vineyard sunset sail with us creates an unforgettable experience — far more memorable than a typical night out.
Spaces are limited, and each sunset is unique — visit our Sunset Sails page for details and to reserve your evening on the water.
Explore the Beauty of the Sea with Sail the Vineyard's Photo Gallery
