Update for 2026: Broad Reach has relocated to Maine and now sails from Kennebunkport and Portland; it no longer operates on Martha's Vineyard. We are keeping this post up as a record of a great island operator. For charters sailing this season, see our sailing guide.
Broad Reach Adventures ran classic sailing trips around Martha’s Vineyard on a traditional sailboat. The trips were simple: out on the water, sails up, and the harbors and coastline going by.
Filmed May 2023The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked October 2026.
From the deck you got a long, slow look at the shoreline, the coves and the harbor towns, a side of the island you can’t see from land. No sailing experience was needed. The crew handled the boat while guests looked around, took photos, or did nothing at all.
Routes usually passed Edgartown Harbor, Oak Bluffs, Menemsha, and other familiar spots around the island. Guests could bring their own food and drinks. Trips were for small groups, so it stayed quiet on board, closer to sailing with a friend than a packed tour boat.