Our Services

2-Hour Harbor Day Sails

Vineyard Haven Harbor Martha's Vineyard

Experience the beauty of the 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 Hours

Up to 6 People

$395

4-Hour Day Sails

Venture outside the inner harbor with us and enjoy more of the coastline and sights of Martha’s Vineyard. Bring your own prepared foods, utensils & alcoholic beverages and enjoy 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 Hours

Up to 6 People

$595 

Sunset Sails & Special Occasions

Sunset sail special occasion birthday anniversary wedding proposal

Sunsets are always special, but when enjoyed from the water aboard a sailboat 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.


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 Hours

Up to 6 people

$450

Fireworks Sail

One Night Only - August 17, 2018

Truly one of the best events of the summer, the Oak Bluffs Fireworks are a Vineyard must! There is no better display than the bursts of color cascading over the water.  Join us for a 4-hour event.  We'll sail from Vineyard Haven Harbor to Oak Bluffs, drop the anchor and offer you a front row seat of this amazing annual fireworks display!

Need to accommodate a large group?

Sail Aboard Our Sister Vessel

Experience the ultimate sailing experience aboard Sea Witch.  Sail to different coves and beaches aboard this luxurious 58-foot LOA ketch.


2-, 4-, or 8-hour day sailing excursions as well as multi-day term charters in the idyllic waters in and around Martha's Vineyard are available for larger groups.