The term “social distancing” will be part of our vocabulary for at least a while to come, and there’s no better way to engage in the practice than heading out on a boat. Some of the finest Northeast and New England anchorages are tailor-made for our current situation, with fresh air, beautiful scenery—and the ability to see as many, or as few, other people as you desire.
Bob Garber, the operations manager at Boston Sailing Center, says Cuttyhunk is not just one of the coolest spots in New England, but along the entire East Coast.
“Cuttyhunk is one of those islands in the world where it’s a spiritual adventure every time you pull in,” Garber says. “I believe the graduating class last year was one person. It is literally a one-room schoolhouse. They have a bit of a marina, but I never go unless I’m completely self-sufficient. They have a pizza place, or somebody’s house who makes pizza, that may or may not be open. The little general store may or may not have anything in it.”
The island is about 580 acres, and the most recent census recorded its population at 52. Cuttyhunk is the outermost of the Elizabeth Islands, which are mostly uninhabited. Compared to tourism-friendly Martha’s Vineyard, which is across Vineyard Sound from the Elizabeth Islands, the place feels quiet and remote. And the channel heading into Cuttyhunk helps to maintain that feeling. It’s narrow and shallow, Garber says. Most powerboat owners should be OK, but sailors need to beware. If your boat has a draft of 5½ feet, he says, be careful; if your draft is 7 feet or more, don’t even bother trying.
Another tip that the Boston Sailing Center gives to cruisers heading for Cuttyhunk: Once you’re through the channel and inside the pond, watch for shoaling at the edges of the mooring area. The space is basically a dredged-out square. Don’t stray too far beyond the moorings and the main channel, or you’ll be in skinny water all too fast. There are about 40 or 50 moorings available on a first-come, first-served basis.
Timing your arrival is also key, because ferries can get in, which means the presence of day-trippers during the summer months. But even so, there’s not a ton of noise. There are no cars on the island. Only golf carts. And even on summer weekdays, there usually are moorings available.
Garber says he likes to go ashore and walk the whole island, an activity that is open to boaters no matter what day of the week they arrive. Seeing the locals in their daily routine is like watching time move at a different, slower pace, a reality that lets visitors quiet their minds as well. “The locals will be down on the dock with oysters and lobster and, depending on what’s growing at any given time, some people have pretty big gardens so they’ll be selling vegetables,” he says. “It’s so laid-back and so tight-knit—it’s a very, very cool place.”
Hadley Harbor, Massachusetts
Hadley Harbor is near the Buzzards Bay entrance to Woods Hole, surrounded by the Elizabeth Islands. Boaters who aren’t simply enjoying the fun of cruising sometimes pull into the harbor to wait out the current at Woods Hole. What they discover is a small harbor with free moorings, and an opportunity to launch the dinghy for a gunkholing tour of endless nooks and crannies.
“Hadley Harbor is one of my favorite places on earth,” Garber says. “It’s heavily wooded around most of it, with the exception of a big estate that has a huge grass area leading up to it. And there are horses running around free on the island. They are owned by the people on the island. I don’t think I’ve ever been there without seeing a half a dozen deer wandering around with these horses. You can be sitting on the hook, and 50 yards away in this massive field with the lawn leading up to the huge home, you’ll see the horses and deer. It’s gorgeous.”
The Elizabeth Islands are mostly uninhabited and closed to the public; the Forbes family owns most of them (Cuttyhunk being an outlier), and uses most of them as private summer retreats. The islands that the family does not use are in a natural state. One of the islands is covered in poison ivy; another is a former leper colony that’s now a bird sanctuary.
“You’re not allowed to get off the boats,” Garber says. “There’s one little island that you’re allowed to step on toward the mouth of the harbor, but it is private property. When you’re there, there are no services, no support, nothing. You pull in, you grab a mooring, there’s a decent holding ground for anchoring, and you are on your own.”
The lack of onshore development keeps the place nice and quiet, exactly the way cruisers looking for solitude like it. Day-trippers do sometimes show up, Garber says, but they don’t stay long unless they’re enchanted by the scenery. As he puts it: “There is no other reason to go to Hadley Harbor.”
Monhegan Island, Maine
As the owner of Hardy Boat Cruises for the past 27 years, Stacie Crocetti can’t count the number of times she has cruised out to Monhegan Island. And every time she’s there, she says, she feels like she’s having an otherworldly experience.
“When you go to Monhegan, it’s like stepping back in time,” Crocetti says. “There’s a small little village where the dock is. Three-quarters of the island is all in preservation and won’t be built on, so you can walk out to the back cliffs and be on almost 200-foot cliffs and feel like you’re in the middle of nowhere without any houses around you. It’s all wild. It’s breathtaking and spectacular.”
Some families have owned or rented the same summer cottages on Monhegan Island for 20 or 30 years, she says. Artists including the Wyeth family and George Bellows spent time ashore trying to capture the beauty. What draws them is not just the slow pace away from mainland civilization, but also the way the island seems to have moods. Weather comes and goes, bringing sun or wind or rain. Whatever it is that day, it envelops the place in a special way. “When the fog lays in the harbor and around the island, you really feel it,” Crocetti says. “There’s a physical sense that you’ve been transported to a different time and space. And I’m a person who goes there every year, multiple times a year. I still feel it. It’s really magical.”
There is perhaps no better place to go this summer by boat, she adds. “You do start to embody the sense of separateness from the modern world,” she says. “It’s a deep sense that you’ve stepped out of life, and I really think people need that right now.”
Shelter Island, New York
The view looking out from the south dining dock at the Shelter Island Yacht Club, on the northeast tip of New York’s Long Island, is in many ways a view of sailing history itself. Back in 1914, designer Nathanael Herreshoff drew a wooden sailboat that became known as the Buzzard’s Bay Boy’s Boat. Today, the yacht club calls the fiberglass version of that boat the H12 (short for Herreshoff 12½), and its fleet of them is more than 70 boats strong. The boats are usually out racing on Saturdays from June to September, filling the waters with an elegance of motion that harks back to another era. Most days, though, the majority of the boats are moored behind the club, creating the kind of constantly moving, yet somehow still seascape that has drawn the eye of painters, photographers and other artists for centuries.
“The boats are timeless in their design with a stable full keel, simple gaff-rig,” says Roger Willey, general manager at the Shelter Island Yacht Club. “They are easily sailed but hard to master.
From the club’s south dining dock, there’s a view of the boats toward the head of Dering Harbor, which, as a village, is as charming as they come. It’s the least-populated village in all of New York State. Fewer than 100 people live there in just a few dozen homes, according to the most recent counts. The nearby hamlet of Shelter Heights is a comparative metropolis with a population that, according to the last census, barely tops 1,000. And unlike Dering Harbor, Shelter Heights has a post office.
If you cruise to Shelter Island to take a look, keep an eye out for Poppy, a Herreshoff 12 ½ that club member Samuel Hird bought in 1974. She was the boat that began the creation of the club’s fleet, and she still races today. “The fleet still has a few wooden H12½s sailing about the boats in Dering Harbor,” Willey says, “but for the most part, is almost all fiberglass.”
This article originally appeared in the July 2020 issue.