Sailing Excursion Services

2-Hour Harbor Day Sails

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Experience the beauty of Martha's Vineyard island as you 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.  


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.


2-hour charters may be scheduled 

any time of day.


2 Hour Charters

Up to 6 People

$395

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4-Hour Day Sails

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Venture outside the Vineyard Haven inner 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.


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.


4 Hour Charters

Up to 6 People

$595 

Book Now

Sunsets & Special Occasions

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Sunsets are always special on Martha's Vineyard, but when enjoyed from the water aboard a sailing vessel they take on a magical quality.  Make a toast to another perfect day in paradise with a sunset sail around the inner harbor. Celebrating a birthday, anniversary or proposal?  Sunset sails are the perfect venue for your special evening. These sailing depart Vineyard Haven Harbor. 


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.


2 Hour Charters

Up to 6 people

$450

Book Now

Fireworks Sail

One Night Only - August 16, 2019

Truly one of the best events of the summer, the Oak Bluffs Fireworks are a Martha's Vineyard must! There is no better display than the bursts of color cascading over the water.  Join us for a 4-hour event.  As we depart Vineyard Haven Harbor, enjoy sailing along the coastline to Oak Bluffs where we'll drop the anchor and offer you a front row seat of this amazing annual fireworks display!  Fireworks begin at 8:00 pm.

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Need to accommodate a large group?

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Call us to discuss options & pricing for groups larger than 6.

We can provide 2-, 4-, or 8-hour day sailing excursions in the idyllic waters in and around Martha's Vineyard for for larger groups in conjunction with Sea Witch, our sister ship.

Call us at 508.923.7177