Boston might be America’s biggest small town, but with so many harborside attractions, it has plenty for boaters.

Waypoint: Boston, MA

History buffs and island hoppers alike will find there’s no shortage of places to explore by land and sea in this city.

The USS Constitution in Charlestown.

The USS Constitution in Charlestown.

It may be steeped in history, but Boston is always evolving, especially along the waterfront. That’s one reason local boaters say they’ll never tire of their homeport. “There’s no need to go anywhere else,” says John Blanken, who’s been plying these waters since he was a kid, first on sailboats, then on power cruisers, including the 48 Sabre he just bought. “I often entertain aboard and I like to take my guests on boat tours of the area. Everybody loves that. I take pictures on these cruises, and friends always want shots with the city skyline in the background. I ordered a gyro for the Sabre just to help me get better photos.”

It’s tough to get a bad shot here in America’s biggest small town. And rest assured your Instagram feed will have depth and variety after cruising one of the oldest cities in the country. But what if you’re on a tight schedule and can tie up only for a weekend? How do you make the most of your time in Boston? According to Blanken and others who’ve been cruising here for decades, a good plan is to do the inner harbor one day and shoot out to the Boston Harbor Islands the next.

Tie up and take public transportation to Fenway Park.

Tie up and take public transportation to Fenway Park.

“Get a slip for the night and try to see it all,” says Blanken of the inner harbor, which spans from the Charles River to the Mystic River, with a lot of developed waterfront in between. Locals encourage visitors to reserve a slip near the action (at Commercial Wharf in the North End or historic Long Wharf, for instance) so they can be a short walk or bike ride away from the city’s high-traffic attractions—places like Faneuil Hall, Quincy Market and the Freedom Trail. Yep, these could be the same landmarks that some skippers toured on a high school field trip years ago, but even if you did Boston as a kid, you’ll find new things today—the Rose Fitzgerald Kennedy Greenway parkland, for instance, which extends from the North End to Chinatown, connecting a relatively new frontier of glass and steel construction known as the Seaport District to downtown.

Near the Seaport District there’s dockage and mooring fields for transient boats, but prepare for a lively stay in this busy harbor. Wakes from passing traffic, which can include everything from passenger ferries and tour boats to tall ships, keep floating docks moving and can make for a bouncy dinghy ride, but the harbor quiets down at night.That’s when the action picks up in the streets as foodies go in search of great dining and beer nerds troll cobblestone streets for local craft brew.

The Old State House is one stop along the Freedom Trail.

The Old State House is one stop along the Freedom Trail.

The next morning, before heading out to the islands, consider a run through the locks and up the Charles River. “The best time of year to cruise there is September,” says Blanken. “Temperatures in the harbor cool down, but it remains warm in the river.” A lot of local boaters like to have lunch while underway, since lighter boat traffic on the Charles makes for easier driving, giving the skipper a chance to relax a bit at the wheel. Near the mouth of the river, passengers can take in Boston to port and Cambridge to starboard, photographing landmarks like the Citgo sign near Fenway Park and the campus of the Massachusetts Institute of Technology.

Thanks to the area’s 35-plus colleges, Boston has a reputation for hitting the books first, goofing off second. But boaters know the city’s playful side. Ken Andrews, 71, has been cruising here since he was 9 years old. He and his wife, Patricia, live in Marblehead, but they keep their boat in Boston Harbor. “We’ll stay aboard for days or weeks at a time,” he says. “There’s always something to do.”

One of the Boston Harbor Islands.

One of the Boston Harbor Islands.

The Andrews make regular runs to the Boston Harbor Islands and encourage visitors to do the same, as the 34 islands that make up this National Park are close to the city yet feel like getaways. His favorites? “Georges, which is about seven miles from downtown Boston, is near the top of the list,” he says. “It’s the most famous of them all, since it’s the site of the Civil War-era Fort Warren.” But if he had to pick just one of these islands to visit, Andrews would choose Peddocks. At 184 acres, it’s the largest island in the harbor and boasts the longest shoreline. It has an interesting history, too. It’s home to the now-defunct Fort Andrews—active in harbor defense from 1904 to the end of World War II—and was also used for filming scenes in Martin Scorsese’s movie Shutter Island. “From here, you also get great views of Boston Harbor,” says Andrews, which could include glimpses of the 496-foot-tall Custom House Tower and Kennedy Library. That’s as picture perfect as it gets.

why-go

Why Go?

Once a barren section of the waterfront packed with parking lots, the Seaport District is now a hot spot with a food scene that sizzles.

Things To Do

z-quincy-market

Quincy Market (above) is just one of the city’s historic landmarks that is within walking distance of slips and moorings in Boston’s inner harbor. Family-friendly ­attractions are near the waterfront, too, including the New England Aquarium on Central Wharf.

This article originally appeared in the September 2018 issue of Power & Motoryacht magazine.

Related