Boaters docked at Constitution Marina have many options within easy reach: step next door to the 305-foot USS Constitution, first launched in 1797; follow a portion of the Freedom Trail to visit landmarks from the American Revolution; or take the kids to the marina pool and introduce them to the famous line, “One if by land, two if by sea.”
“We have the history of Boston,” says Tom Cox, the marina’s general manager and co-owner. “During this 250th anniversary, you can sit at our pool and look out over the river where Paul Revere once rowed.”
With the country marking its anniversary, cruising to Boston is especially rewarding. The city blends deep historical roots with modern amenities, making it one of New England’s most inviting and sophisticated boating destinations. Decades ago Boston Harbor was notorious for pollution—once called the “dirtiest harbor in America” in the 1980s—but a multibillion-dollar cleanup transformed the shoreline. Today people swim, fish and enjoy coastal recreation, and Boston’s coastline ranks among the cleanest urban beach networks in the United States.
“It’s gone through a renaissance,” Cox says. “Now Boston is a destination on par with Newport and Nantucket, but we offer something different—more variety for boaters.”
Constitution Marina’s leadership brings deep local knowledge. Co-owner Peter Davidoff’s family began a small marina on Lewis Wharf in the 1960s. That modest facility—initially serving roughly 15 boats—moved in the 1970s to the larger site that became today’s Constitution Marina, a nearly 300-boat facility that welcomes transient cruisers into the heart of Boston’s waterfront community.
“One of the things that makes Boston special is its mix of people,” Davidoff says. “Boating in Newport and Nantucket is often seen as very upscale. Boston includes those communities but also blue-collar residents; some people actually live on their boats here.”
Cox adds that Constitution Marina hosts the largest liveaboard community in New England, which says a lot about both the marina and the city. “Residents don’t need a car—everything is walkable. From here you can reach restaurants, ballgames and theaters on foot,” he notes.
There’s plenty to explore on Boston’s waterfront. Constitution Marina sits beside the home of the USS Constitution, nicknamed “Old Ironsides,” launched from Edmund Hartt’s Shipyard in 1797 and open for tours alongside the USS Constitution Museum.
“If the Constitution were any closer, she’d be renting space from us,” Davidoff jokes. “The U.S. Navy keeps her in impeccable condition. She’s an active commissioned warship—the oldest in the world—and one of the tallest of the tall ships.”
Constitution Marina is also about a 10-minute walk from TD Park, home to major sports and concert events, and a 15-minute walk puts boaters in the heart of downtown. Visitors can tailor their Boston experience—tour historic sites like the Old North Church and Faneuil Hall, or simply wander the neighborhoods and sample the city’s dining and cultural scene.
Cruising Boston Harbor is a highlight. Cox and Davidoff are active boaters—Cox keeps a Hudson Force 50 sailboat, a 35-foot Island Gypsy trawler and an O’Day 23 keelboat, while Davidoff owns a Jeanneau 51 monohull—and they regularly explore the harbor and its roughly 34 islands. The harbor offers protected anchorages where conditions inside can be calm even when the outer waters are rough.
“Even with 4- or 5-foot seas outside, it can be flat as a pancake in the islands,” Cox says. From Constitution Marina a day sail can reach historic Massachusetts ports such as Marblehead, Salem and Gloucester—each with its own maritime legacy from the nation’s earliest years.
Boston’s streets and waterfront reflect its long maritime history; the city’s layout—with narrow, winding roads and old pathways—feels more like an ancient European port than a grid-planned metropolis. “Boston has charm, culture, great restaurants and world-class education,” Cox says. “Come by boat—you’ll be better off without a car. Walk the city and enjoy it.”
For the 250th celebration, Davidoff plans to anchor out to view the tall ships, while Cox will watch from the marina. Afterwards they’ll likely dine at one of the nearby newer restaurants, such as Prima Boston, which Cox recommends for steaks and pasta.
Cox also praises longtime local favorites like the Warren Tavern, a centuries-old establishment tied to Revolutionary-era patriots such as Dr. Joseph Warren. The marina provides transient boaters with a welcome packet that includes restaurant discounts and information on nearby attractions like the Museum of Science.
Visitors may stay a few hours, several days, or longer. The marina is just a short walk from a dog-walking park for cruisers traveling with pets, and the facility offers about eight rentable “bed-and-breakfast” style boats for overnight guests. “Someone with a 25-foot boat can put relatives on one of our B&Bs and everyone can go exploring,” Cox says. “My family loves sitting on those boats and watching the harbor lights.”
Constitution Marina continues to upgrade its docks and amenities, while maintaining a consistent service philosophy. “We’ve had the same approach for years,” Cox says. “We make it fun and easy for people to enjoy their boats. That’s what we do.”
This article was originally published in the August 2026 issue.