Sailing Martha's Vineyard — Charters, Lessons and Harbors

Why Go Sailing on Martha's Vineyard

• Coastal views you can't get from shore, plus beaches you can only reach by boat
• A long maritime history you can still see in the working harbors
• Cruises if you want to sit back, lessons if you want to steer
• Four harbor towns to sail between, each with its own docks and restaurants
• Marine wildlife sightings are common along the way

Featured Local Partner: Cheap Therapy Charters

Cheap Therapy Charters is a family-run local business we're glad to feature. They run customizable charters — harbor cruises, sunset sails, bachelorette outings, island trips, and fishing runs. A good fit for families and groups who'd rather have a local captain than a big tour boat.

Popular Sailing Destinations

• Edgartown Harbor: The lighthouse, old whaling captains' houses, and plenty of restaurants near the dock.
• Menemsha: A working fishing village; people line the beach every evening for the sunset.
• Vineyard Haven: The island’s main port — shops, marinas, and most of the boat traffic.
• Oak Bluffs:Gingerbread cottages, a busy harbor, and the island's nightlife.

Sailing Conditions and Best Times to Sail

The sailing season runs from late May through early October. Expect warm days, steady breezes, and calm evenings — good conditions for daytime charters and sunset cruises alike. Check the local forecast and tide charts before heading out.

Sailing Options for Visitors

• Chartered Cruises: A local captain handles the boat; you need no experience.
• Sailing Lessons: Island instructors teach courses for all ages and skill levels.
• Boat Rentals: If you already sail, rent a boat and set your own route.
• Sunset & Specialty Cruises: Popular with families and for celebrations on the water.

Sailing Safety and Regulations

Know the local navigation rules, weather patterns, and safety requirements before you go. The U.S. Coast Guard Boating Safety site has the details.

Local Sailing Schools and Clubs

Two local options for lessons, racing, and meeting other sailors:

• Sail Martha's Vineyard : Classes and camps for all ages and experience levels.
• Vineyard Haven Yacht Club : Sailing programs, regattas, and community events.

Sailing is how a lot of us prefer to show people the island — the shoreline reads differently from the water. Book a charter if it's your first time out, or take a lesson and come back next summer able to handle the boat yourself.

→ More guides below: outdoor activities, dining, and other things to do on Martha’s Vineyard.

More photos: our sailing gallery.