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

Don' forget the ship's rations! Gourmet hors d'oeuvre or dessert platters are available 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 Charters

Private, Up to 6 People

$775

If you just live to be on the water like we do, a Martha's Vineyard boat charter of only 2 or 3 hours 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 Charters

Private, Up to 6 People

$900

Sailing trips from 5-8 hours are also available.  Call for details and pricing.

Don' 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 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..

  Have you ever noticed that sunsets are different from one place to another? You may notice more red and orange hues in the Caribbean, perhaps more lavender and violet or even brilliant blue around Cape Cod. 

From the water, there is a decidedly magical quality; a Martha's Vineyard sunset sail takes the magic to another level. Designed to be a more low-key, relaxing and leisurely sail, our sunset sails ae perfect for those seeking romance, too. Celebrating a Cape Cod elopement, Martha’s Vineyard wedding, birthday, anniversary or marriage proposal? A sunset sail Martha’s Vineyard style is 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 learn more about our 

Public "By The Ticket" Sailing Options

Bring along your favorite bottle of white or sparkling white wine and add on our famous gourmet hors d'oeuvre platter to compliment your perfect evening on the water.  You'll be able to add it to your cart during the reservation process.