Most people who sail here go out on a charter: someone else runs the boat, there is a snack board on deck, and the island goes by from the water.
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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
A harbor full of sailboats on their moorings on a summer morning, before the wind fills in.
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 on a restored 28-foot Bertram powerboat (harbor and sunset cruises, beach and sandbar days, 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 brings warm days, steady breezes and calm evenings, good for daytime charters and sunset sails.
It is worth checking the local forecast and the tide charts before you go out; conditions here can change faster than the day suggests.
You will want to 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.
A charter is the easy way to go out the first time. A lesson means you can come back next summer and handle the boat yourself.
Keep Reading
Keep exploring
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