Private Sailing Charters on Martha's Vineyard Island: "Just You & Me & The Sea"

 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

$625

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.

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

$775

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

$900

Call for details and pricing for excursions longer than 4 hours.

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..