Skip to main content

Chartering New England

This is the beginning of one of the country’s—no, the world’s—great cruising grounds, stretching from the tip of Long Island Sound all the way up the Maine coast to the Bay of Fundy.  

To the uninitiated, chartering a boat in southern New England doesn’t have anywhere near the same romantic appeal as, say, sailing in the Caribbean. But once you’ve bitten the proverbial bullet and booked a boat there anytime between late May and the end of September, you’ll know why the local sailors love these waters so much. This is the beginning of one of the country’s—no, the world’s—great cruising grounds, stretching from the tip of Long Island Sound all the way up the Maine coast to the Bay of Fundy.

Leaving Maine out of the equation this time around, your only problem will be narrowing down the area you want to visit. Since bareboat charter companies are concentrated south of Cape Cod, that decision is kind of made for you. I say “kind of” because the Cape and Islands offer more beautiful anchorages and attractive destinations than could ever be squeezed into a week’s cruise, and though most of Long Island Sound is kind of dull, there are some very pretty harbors there too.

Take a boat out of Newport, Rhode Island, and once you’ve sailed past Newport’s waterfront mansions and out of Narragansett Bay, you can head for Cuttyhunk and the Elizabeth Islands, Martha’s Vineyard and Nantucket; if you’ve elected to charter out of Mystic, Connecticut, the welcoming embrace of Block Island’s Great Salt Pond is only a few hours away, and from there it’s a logical hop to the tip of Long Island and the delights of Sag Harbor. From there, a leisurely sail across Long Island sound takes you to the beautiful harbors of Essex and Stonington. Wind up the week with a visit to Newport.

For me, the real heart of southern New England cruising is Buzzards Bay, where the breeze honks up to 15-20 knots on summer afternoons, offering glorious sailing and a great choice of anchorages and harbors to duck into when the sun gets low—New Bedford, Padanaram and Marion on the western shore; Cuttyhunk or one of the other Elizabeths to the east.

Most of this little island chain is owned by the Forbes family, but there’s no restriction on anchoring off them—Hadley’s Harbor, on Nonamesset Island, is especially lovely. Cuttyhunk’s inner harbor gets crowded on summer weekends, but there’s a great anchorage outside. If you’re lucky, the famous Raw Bar boat will raft up alongside, and the crew will shuck as many oysters as you can eat for your evening appetizer.

The time will come when you want to slip through the islands and head for Martha’s Vineyard, which will require you to experience the full force of the tidal current as you slip through Woods Hole, a small gap between the mainland and the Elizabeths. You’ll have little time to check out the famous oceanographic institute as you ride the current that rips through this tricky dogleg at up to 6 knots—it’s a bit of a buttock-clenching experience the first time you do it!

Everyone anchors or picks up a mooring at Vineyard Haven on Martha’s Vineyard, and with good reason—it’s the epicenter of the island’s maritime life. Should you tire of the bustle and you draw south of 6 feet, slip into Lake Tashmoo, but make sure your anchor is well set. It’s easy to embarrass yourself in this shallow anchorage, but once dug in, it’s a great spot to enjoy a gorgeous New England sunset and a quiet night.

From there, be prepared to face yet more choices. Do you cross over to the mainland and visit Hyannis? Head for Nantucket for a dose of history and a chance to mingle with the rich and famous? Or just daysail out of the Vineyard and enjoy some lazy beach days? The waters south of the Cape are warmed by the Gulf Stream, making swimming an altogether more enjoyable experience than in the frigid waters of Maine. (Don’t let the fact that Jaws was filmed on the Vineyard put you off).

All in all, the sometimes challenging currents and the robust sea breezes make chartering in these waters ideal for more experienced sailors who are after a memorable boating experience. Call me biased, but I love sailing in New England.

Photos by Peter Nielsen

Read about more charters in the United States:Chesapeake BaySan FranciscoGrand Traverse BaySan Juan

For highlights, advice and charter company links go to:Five Charter Destinations in the United States



Crowdsourcing Age-of-Sail Weather Data

Although big, multi-million-dollar projects like the Large Hadron Collider and the human genome project with their legions of PHD’s tend to grab headlines, there’s still a part of play for the “citizen scientists” of the world. Amateur birders have long contributed to an more


Ultims to Race Solo Around the World

For years now, maxi-trimarans, both solo-sailed and fully crewed, have been racing the clock on their own around the world in an effort to set ever faster records for the world’s fastest circumnavigation under sail. Back in 2000-01 there was also a no-holds-barred more


Juneteenth on the Water

Discovering Amistad and Mystic Seaport Museum have partnered to organize their third annual Juneteenth festival, featuring concerts, speakers and a reflection on the lasting legacy of racial injustice in America. Declared a National Holiday in 2021, Juneteenth celebrates the end more


New Multihulls for 2022

Lagoon 51 In keeping with many of the more recently launched models created by French multihull builder Lagoon, the Lagoon 51 is all about comfort, “en plein air,” in particular, as the French might say. Topside, a whopping 80 percent of the boat’s flybridge is given over to more


How to Spectate on the Newport Bermuda

The biannual Newport Bermuda Race starts on Friday with the first warning signal at 1 pm. Whether you’re tracking a loved one’s progress or just spectating an event that draws pros and weekend warriors alike, there are plenty of ways to stay up to watch. The starting line will more


US Sailing Strikes Gold in Hyères

After being skunked or nearly skunked at multiple Olympiads, could the US Sailing Team (USST) now under the direction of Olympic veteran Paul Cayard, be finally turning it around? If its performance at the 53rd French Olympic Week regatta in Hyères, France, where the team posted more


New York City’s Newest Fleet

120 children enrolled in Brooklyn Boatworks’ STEM and life skills-focused program launched their hand-built optimist prams on June 14 from Pier 2 in Brooklyn Bridge Park. The launch is the culmination of years of student work, with boats in process before the pandemic caused the more


Charter: Off the Beaten Path

So, you like to charter in the Caribbean with its warm waters, swaying palm trees, steady trade winds and strong rum drinks. What’s not to love? It can be easy, though, to get stuck in a rut when chartering year after year in the same place. Sure, the British Virgin Islands are more