Some of the best cruising grounds in the U.S., if not the world, are found off the south shore of Cape Cod and the nearby islands – the Elizabeth Islands stretching southwest between Buzzards Bay and Vineyard Sound, and then Martha’s Vineyard and Nantucket offshore. Here’s a look at 16 great cruising destinations there from New England Boating. You can easily cruise to two or three of them (or more) in the same day, but each one is worth a long visit in its own right.
First on their list is Cuttyhunk, as it would be for mine too, not only because it’s the first stop on the Elizabeth Islands for anyone cruising up from Long Island Sound, Newport or Block Island, but also because it is an absolutely iconic boating destination. One warning: Forget about it in the fog or restricted visibility, because the entrance is narrow and can be sketchy. But if you’re a normal human being, once you’re inside the protected harbor your blood pressure will drop 20 points, and you can totally relax at a mooring or dock. Make sure you climb up the hill for fantastic views of both Buzzards Bay and the mainland in one direction and Martha’s Vineyard in the other. Back on the water, call Cuttyhunk Shellfish Farms; they’ll deliver fresh oysters to your boat.
Second on my list, and third on New England Boating‘s, is Menemsha, on Martha’s Vineyard just across the sound from Cuttyhunk, a small harbor with a working commercial fishing fleet (and great take-out seafood shacks on the dock) and a dock and mooring balls (pictured above). Menemsha also has a gorgeous white-sand beach. In case it looks familiar, some of Jaws was filmed there, as well as other places on Martha’s Vineyard. I personally would recommend an overnight in Cuttyhunk and then a long, very relaxed weekend in Menemsha, catching some rays on the beach, enjoying some local galleries, and gorging on lobster rolls from Larsen’s Fish Market on the dock.
After that, it’s a free-for-all, with larger tourist destinations including Oak Bluffs, Vineyard Haven and Edgartown on Martha’s Vineyard. If you up to Edgartown think about cruising to East Beach on Chappaquiddick, accessible only by four-wheel drive vehicles or boats. It’s long, it’s remote, and it’s beautiful.
My personal favorites after that are the Nantucket Boat Basin, where I could easily spend on entire summer (I haven’t been able to pull that off yet, but there’s still time) or the totally laid-back harbor of Madaket on the west end of the island. The channel going in is winding and the water can be thin, but you won’t find any crowds, just old Nantucket summer cottages. There’s a reason Mister Rodgers made it his summer neighborhood for more than 30 years. For more: