Like you, we consider a lot of boating destinations our favorites. Choosing top cruising locales can feel an awful lot like pinpointing a favorite boat. But we have to do the deed as we celebrate Soundings’ 60th anniversary. So here, we offer a look at six destinations that we believe have most stood the test of time with generations of boaters. Yes, they’re all in New England, but that’s because that corner of the world was home port to Soundings when it was first launched, and the region remains close to the hearts of many of the people who continue to read and enjoy the magazine today.

Block Island, RI

Henry DuPont, who runs Block Island Community Sailing and has lived on the island for 50 years, says there’s a simple reason that boaters love to return again and again. “The Great Salt Pond is one of the most fabulous, scenic and comfortable harbors in New England. It’s just great,” he says. “We can have 800 boats in the pond and in the marinas, and it’s all people enjoying the cruising lifestyle.”

Boaters are, in a nutshell, the beating heart of this island. On a typical summer day, DuPont says, at least a third of the people on and around the island are staying overnight on boats. “Years ago, we saw more of the Sparkman & Stephens kind of boats here, those beautiful 50-foot yawls. They’ve been replaced with boats that are more high-performance, and that’s okay,” he says. “There are still many classic boats that come out.”

Kate McConville, the harbormaster in New Shoreham, says one of her favorite things about Block Island is that in the 30 years she’s been coming here, nobody has let the big chain restaurants or stores encroach on the classic New England charm. “Block Island is busy in the summer, but we don’t get the cruise ships. It’s not like other places that are overrun,” she says. “You can go to the same T-shirt shop or into the same little souvenir store selling the sand in the bottle. Even my family, when they come to visit me, they have their traditions. They want to go to that same restaurant and get that same clam chowder or lobster roll. These places have stayed the same.”

In fact, she says, many of the people who help to run these places during the summer season are boaters who’ve been coming to the island for decades. “We have a boating community that lives on their boats and works at all the restaurants and shops during the summertime,” she says. “Housing is a big issue out here, so boating is a little cheaper.”

During big holiday weekends, McConville says, as many as 1,200 boats can pack into the Great Salt Pond’s marinas, private moorings, town moorings and anchorage. Average summer weekends tend to see 700 to 800 hulls on the scene. DuPont says plans are in the works to build a maritime welcome center near the boat basin. Fundraising is happening now. “We’re going to build a fabulous facility with a dinghy dock, hot showers, a laundry, a general-purpose room with Wi-Fi and all the other amenities,” he says.

One of DuPont’s favorite times of year is Block Island Race Week, over the Memorial Day holiday. “There are some fabulous boats that come out to race,” he says. “It just couldn’t be nicer.” 

Newport, RI

Many of today’s boaters know this bustling port city as the home of the Newport International Boat Show, but from 1930 through 1983, it was home to America’s Cup racing, which created a culture of boating that remains as much a fixture as the docks along the harbor.

“I was just talking to this gal who works for Morgan Stanley, and I asked her if she knew anything about Newport, and she said she was there in 1983 when we lost the Cup,” says Charlie Dana, former owner of what is now Safe Harbor Newport Shipyard. “Some of the people who were around in those days said that defeat was the end of Newport. But it didn’t turn out that way. It turned out a lot better than that.”

The loss of the Auld Mug was a tough one for the city to stomach after so many years of being associated with winning the races, says Dana, who has made his home here since 1977.

“I remember in ’77, getting into a cab at La Guardia airport in New York, and the driver asked me how the races were going up in Newport,” Dana says. “That’s what these guys did for the city and for that sport.” Since then, the sailing spirit has endured and even evolved despite a significant increase in powerboats on the local waters. The New York Yacht Club, despite losing the cup, increased its presence by developing the Harbour Court facility for its members while the Ida Lewis Yacht Club remains the place where the local sailors, the longtime representatives of the city’s maritime culture, continue to go. Meanwhile, the waterfront is thriving with shops and restaurants, many with a nautical flair.

“At one point, we were all a little worried,” Dana says. “You could row out in Newport Harbor in a little boat and look back, and some of the timeshare and condo developments along the waterfront would make you depressed. You’d think, ‘This harbor has had it.’ But right in the ashes of what was going on with mansion development, there were positive signs popping up. There was the Museum of Yachting, and then Harbour Court comes along. It was extremely important to Newport, because you had the yacht club members coming up and changing the culture.”

The IYRS School of Technology and Trades is now here (and has been since back in the days when it was still known as the International Yacht Restoration School). The National Sailing Hall of Fame is a landmark too, celebrating the heroes of the sport.

“It’s an incredible harbor. It has history. It has museums. It has everything,” Dana says. “And it still has a wonderful feeling. You go to places like the Cooke House and the Candy Store, and some of them feel more like clubs than Harbour Court. It’s great to see all of the people from the sailing world, surrounded by pictures from the great moments of sailing.”

Nantucket, MA

The Nantucket Boat Basin has remained a favorite destination for generations in part because it’s so convenient to other great stops for cruising boaters. From Hyannis, the jaunt to Nantucket is 26 nautical miles. From Newport, it’s 71. Block Island is about 80 nautical miles away and Montauk is barely 90.

Check-in time on the docks at the Nantucket Boat Basin is after 1 p.m., which is why, on a lot of summer afternoons, the Nantucket Whaling Museum sees an influx of visitors. “If somebody’s passionate about maritime, they’re making a stop at our museum,” says Ashley Santos, the museum’s director of marketing and communications. “We’re so central, right by the docks. It’s a really easy thing for visitors to walk over to from their boats.” Whaling, of course, is the type of boating that originally built Nantucket into a thriving community. Between 1750 and 1850, nobody would dare describe North America’s major whaling ports without including Nantucket on, and sometimes at the top of, the list.

Today, it’s Nantucket’s Race Week that brings lots of boaters together every August, but all throughout the summer, Santos says, the area is filled with every type of boat a yacht-spotter could imagine. “The harbor is chock-full of all kinds of vessels in the summer,” she says, adding that as with other popular destinations, the boats only keep getting bigger. “There are many private boats that come to the island, and it’s not unusual to see three or four huge yachts right outside the harbor because they’re so big, they can’t even fit inside.”

The essence of Nantucket, she says, can be felt in all kinds of surprising places today—including at the Macy’s Thanksgiving Day Parade, held each year in the heart of New York City. Starting this Memorial Day, the Nantucket Whaling Museum will open its exhibit about Tony Sarg, who created the parade’s famous balloons.

“Sarg always summered on Nantucket,” she says. “This island has so many ties to New York. In fact, the original founder of Macy’s was also from Nantucket.” 

Cuttyhunk, MA

Manhattan also earns a mention in the history of this outermost of the Elizabethan Islands. “The island really began as a fishing destination for bigwigs in New York City,” says Robyn Weisel, director of the Cuttyhunk Historical Society. “Businessmen came out to the island looking for striped bass. There was a fishing club, and it still exists today.” Cuttyhunk was, and is, beloved because it’s kind of incognito, she says. “Even people who live seven miles off the coast in New Bedford don’t know where Cuttyhunk is.”

U.S. presidents have come and gone, including Ulysses Grant and Chester Arthur. The latter “was perhaps the most avid angler ever to hold the title of commander in chief,” according to the society’s records. “He visited Naushon and fished from the Cuttyhunk Club for a week in 1882.”

Today, it remains true that having a summer home at Cuttyhunk is a mark of affluence. Unlike in other popular destinations throughout New England, it can be hard to find a rental here. “You have to know a family member or something like that,” Weisel says. But those who visit by boat—she’s counted about 100 vessels in the inner harbor at one time in summer—sometimes get treated to serious celebrity spottings. Back in the day, when the Allen House still served lobster and steak, Jackie Onassis paid the place a visit. Her feet quickly became a hot topic of discussion around town.

“A lot of people on the island don’t wear shoes. Especially residents. It’s kind of like an ‘in’ thing where you can tell the residents apart from the tourists,” Weisel says. “She must have caught onto this trend because she came to the Allen House with no shoes on—but it was the one place on the island where you actually had to wear shoes to enter the building. Nobody wanted to be the one to tell her, but somebody eventually went up to her, and she sent somebody out to her boat to go get her shoes.”

Because Cuttyhunk remains so unspoiled it remains a must-stop for boaters cruising around New England, trying to see the best of the best locales. “People think they’re in the ‘in’ group when they come to Cuttyhunk,” Weisel says. “They think it’s a find that not a lot of other people know about. It’s so under the radar, it’s really a boaters’ paradise.” 

Mystic & Stonington, CT

By far, the best-known attraction for boaters in this part of Connecticut is the Mystic Seaport Museum. But it’s not just the experience of being at the museum that makes the destination so special, says Chris Gasiorek, who is vice president of watercraft preservation and programs. It’s also the experience that cruisers have getting there. “When you come into Fishers Island Sound, the view is the same as it was 100 years ago,” he says. “You see the lighthouse, the village, the Mystic River Bascule Bridge. What’s neat about this area is that a voyage into Mystic really feels like it did five or ten decades ago.”

Of course, some things have changed—the museum has updated its marina with floating docks and showers, as just one example—“but the feel of the museum, the experience of walking around at night when only boaters have access, that’s as close to time travel as you can get,” he says. “We have grandparents bringing their kids on boats because the grandparents remember being there when they were kids.”

In the village of Mystic, downtown shops and restaurants have a nautical feel, with Abbott’s Outpost serving hot lobster in the same style that makes the original location in Noank a perennial fan favorite.

Nearby in Stonington, Gasiorek says, the destination also keeps luring boaters back because it seems so familiar. “Geographically, it doesn’t have any opportunity to change, so it really feels the same,” Gasiorek says. “The whole of Fishers Island Sound, the beaches you can go to on day trips, it’s like a little bit of Maine stuck between Boston and New York. It has that feel, sort of a rocky coastline. It’s a different view geographically with great little places to stop.”

One of the things boaters love to do at the museum in Mystic, he says, is order “off the menu” for a special tour of the collection of boats inside Mystic Watercraft Hall. It won’t officially open to the public until at least 2025, but he says it has long been an insiders’ secret that tours are available for visitors who ask. “It’s in a warehouse across the street. It’s about 470 boats,” he says. “We have Laser number zero, a couple of Chris-Crafts and Donzis, and President Roosevelt’s boat. Do you remember the end of Raiders of the Lost Ark, where they go into that warehouse and it goes on into infinity?” he adds. “It’s like that, but with boats.” 

Montauk, NY

Clint Bennett is the 14th generation of his family to be working Montauk’s waters as a fisherman. “My family dates back to the original settlers with the natives,” he says. “They’ve been on boats ever since they could dig them out of trees here.” The place doesn’t change much, he says, because there’s less than 3 miles of land between the ocean and the bay. What’s there is there, and there’s not much room to squeeze stuff in, which means any possible sprawl of development is kept to a minimum.

All kinds of boating happens in Montauk, but it’s fishing that has cemented the village’s reputation as a must-visit boating destination. Located way out on the tip of Long Island, Montauk’s surrounding waters have always been teeming with fish. In the summer months, some of the best sportfishermen in the world congregate here, prowling the area for marlin, wahoo and dorado. Around about August and September, it’s not uncommon to see so many tuna and sharks that they’re practically leaping out of the water.

“There’s a whole salty atmosphere when you’re out here,” Bennett says. “It’s not surprising some of the biggest northern Atlantic tournaments are held in Montauk.”

Bennett keeps things fairly simple aboard his 19-foot Privateer center console. He’ll take it out in the bay or the ocean, sometimes going for fish, and other times grabbing up shellfish. A lot of the local boats are like his, he says, even though the boats owned by transients keep getting bigger and bigger. At least 90 percent of them, he says, come to Montauk to fish the offshore canyons. “The boats come from all around the world,” he says. “The biggest one I’ve seen this year is 160 feet. They couldn’t get it in the harbor. The crew had to anchor outside, and they tendered back and forth.”

Locals run their own boats or take guests out charter fishing, and the commercial fishing fleet can be seen doing its thing for miles. At various times of the year, Bennett says, he’ll see anywhere from just a few boats to more than 3,000. More than a few of them call on Bennett and his wife, Kimberly, for the clam and lobster pies, and fresh-caught oysters, that they sell out of their home.

“The boaters reach out to us every year,” Kimberly says. “They’ll pull into Montauk and enjoy our seafood, our incredible trails to hike and bike, restaurants and great nightlife. It’s a teeny-tiny town, but it has a lot to offer.” 

This article was originally published in the April 2024 issue.