“Social distancing” has entered our everyday vocabulary, and one of the safest, most restorative ways to practice it is by heading out on the water. The Northeast and New England coastlines offer many anchorages that are ideal for socially distanced boating—fresh sea air, dramatic scenery, and the choice to encounter as many or as few people as you prefer.
Cuttyhunk, Massachusetts
Cuttyhunk stands out as one of New England’s—and the East Coast’s—most singular island destinations. Bob Garber, operations manager at Boston Sailing Center, describes it as a place of quiet charm and rugged simplicity. The island’s community is tiny: roughly 580 acres and a most-recent census population of just 52. Unlike busier nearby islands, Cuttyhunk feels remote and unhurried, where daily life moves at a slower pace.
The approach into Cuttyhunk reinforces that sense of seclusion. The channel is narrow and shallow: most powerboaters will manage fine, but sailors should be cautious. Boats with a 5½-foot draft should proceed carefully; vessels drawing seven feet or more should avoid attempting the channel. Once inside the pond, beware of shoaling near the mooring edges—the sheltered mooring field is essentially a dredged square, and venturing beyond the marked moorings and main channel can quickly lead to skinny water.
There are approximately 40 to 50 moorings on a first-come, first-served basis. Timing your arrival is important in summer, when ferries bring day-trippers, but even during peak season the island remains peaceful: no cars, only golf carts, minimal nightlife and usually available moorings during weekdays. Shore visits reward boaters with island life—locals selling oysters, lobster and seasonal produce, and quiet walks around an island that feels like a step back in time.
Hadley Harbor, Massachusetts
Located near the Buzzards Bay entrance to Woods Hole, Hadley Harbor is a favored stop for cruisers waiting out current at Woods Hole. The harbor offers free moorings and excellent dinghy gunkholing—narrow coves and sheltered inlets perfect for exploring by tender.
“Hadley Harbor is one of my favorite places on earth,” Garber says, noting the thick woods, open lawns and the spectacle of free-roaming horses and deer that sometimes graze nearby. The natural setting is largely untouched; many of the Elizabeth Islands are privately owned and closed to the public, which keeps development minimal and the harbor serenely quiet.
There are few services here—no provisioning or support—so visitors must be self-sufficient. Anchoring and mooring are straightforward, with decent holding ground, and the lack of onshore activity is exactly what sailors seeking solitude appreciate. Day visitors do arrive occasionally, but they rarely stay long unless the scenery captivates them.
Monhegan Island, Maine
Monhegan Island delivers a distinctly otherworldly experience. Stacie Crocetti, owner of Hardy Boat Cruises, says visiting Monhegan feels like stepping back in time. The island’s small village clusters around the dock, while roughly three-quarters of the island is preserved and protected from development, offering raw cliffside beauty and sweeping coastal views.
Visitors can walk to 200-foot cliffs and experience a landscape that feels untouched by modern life. Monhegan has long attracted artists and families who return year after year—partly because the island seems to have distinct moods as weather and light shift, wrapping the place in fog, sun or wind that intensifies its sense of isolation. For boaters seeking a true escape from the mainland, Monhegan is especially compelling this season: the island’s preserved nature and small-boat access create a powerful feeling of separation from everyday concerns.
Shelter Island, New York
Shelter Island, at the northeastern tip of Long Island, combines maritime history and serene harbor scenes. The Shelter Island Yacht Club’s south dining dock looks out over a fleet of Herreshoff 12½s—classic designs that trace their roots to early 20th-century yacht design. These nimble, graceful boats still race in the summer and create a timeless seascape when moored in Dering Harbor.
Roger Willey, general manager at the club, notes that the H12s are simple to sail yet rewarding to master, their full keels and gaff rigs contributing to a historic aesthetic on the water. The village of Dering Harbor is one of New York’s smallest communities—fewer than 100 residents in a cluster of homes—while nearby Shelter Heights has a slightly larger population and basic services like a post office. Look out for Poppy, a Herreshoff 12½ purchased by a club member in 1974 that helped launch the club’s fleet and still races today.
These anchorages—Cuttyhunk, Hadley Harbor, Monhegan Island and Shelter Island—offer boaters varied opportunities for socially distanced cruising, from quiet sheltered moorings and secluded hiking to dramatic coastal views and maritime tradition. With careful planning, self-sufficiency and respect for local rules and private property, these New England and Northeast havens deliver safe, restorative escapes on the water.
This article originally appeared in the July 2020 issue.