Most people who sail here are not sailing. They are sitting on someone else’s boat with a cheese board, watching the island go past from the side you cannot see from the road.
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Sailing is how a lot of us prefer to show people the island. The shoreline reads differently from the water, and there are beaches out here you cannot reach any other way.
Why go sailing here
Where people sail to
Forty-odd hulls on moorings before the wind fills in. By afternoon most of them are somewhere off the north shore.
How to get out on the water
A local charter we are glad to point to
Cheap Therapy Charters is a family-run local business. They run customizable trips (harbor cruises, sunset sails, island runs and fishing outings) and they suit families and small groups who would rather have a local captain than a big tour operator. Read more about them.
Know Before You Go
Before you cast off
Late May through early October: warm days, steady breezes, calm evenings. Good conditions for both daytime charters and sunset sails.
Look at the local forecast and the tide charts before you go out. Conditions here change faster than the day suggests.
Know the local navigation rules and safety requirements. The US Coast Guard boating safety site has the detail.
Sail Martha’s Vineyard runs classes and camps for all ages and levels.
The Vineyard Haven Yacht Club runs sailing programs, regattas and community events.
Book a charter if it is your first time out, or take a lesson and come back next summer able to handle the boat yourself.
Keep Reading
Keep exploring
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