Your Boston Waterfront Weekend Is Waiting

Sponsored by Meet Boston

Feeling the breeze coming off Boston Harbor on a fine summer day, first you’ll get that hit of sea salt, along with the welcome coolness of air that’s rolled in from the North Atlantic. But breathe deep, and you may find the wind stirs up something else. Maybe it’s a sense of thrill, bringing thoughts of casting off for adventure. Or maybe it’s a calming-down, a relaxing into the waterfront vibe, having endless sparkling waves as a backdrop for strolls, cocktails, concerts, or whatever catches your fancy.

Curving around one of the finest natural harbors in the world, and extending inland along scenic ribbons of river, the Boston waterfront has long been a place where journeys begin. What yours will be like is up to you—the options are endless, and the breeze is calling.

Hit the Water

Islands and lighthouses rank high on almost every visitor’s New England bucket list, and one of the best places to check off both is Boston Harbor Islands National and State Park, a stunning collection of 34 islands and peninsulas. Ferry service from Long Wharf runs from May to October; for a more in-depth look at the harbor and its gems, hop aboard a two-hour narrated Lighthouse Tour led by park staff and Coast Guard volunteers.

Long Wharf bustles with all kinds of on-the-water adventures thanks to the presence of Boston Harbor City Cruises. It operates the Boston Harbor Islands ferry, but also harbor tours, lunch/brunch/dinner cruises, and sunset cruises. Thrill-seekers can get revved up on the cruise line’s Codzilla motorboat, which rockets around Boston Harbor at speeds of 40 mph, or board a high-speed catamaran to see the world’s largest mammals up close during the New England Aquarium Whale Watch Cruise. Venture farther afield with a day trip to Cape Cod on the Provincetown Fast Ferry—a summer destination so popular that there’s a second ferry operator, Bay State Cruise Company, running P-town service from the nearby Seaport District.

Other tour companies along the waterfront put their own spin on seafaring fun, such as Classic Harbor Line’s schooner expeditions on the 80-foot Adirondack III or the 90-foot Adirondack IV. Another voyage into the golden age of sail can be found at Liberty Fleet of Tall Ships, whose reproduction wooden schooner, the Liberty Star, is awash in 19th-century romance.

Those who want to try their hand at the helm can check out short-term instruction and tours at Boston’s top-notch boating schools. Courageous Sailing and Boston Sailing Center, for instance, both offer two-hour private keelboat lessons in Boston Harbor. Over on the Charles River you’ll find Community Boating Inc., the nation’s oldest public sailing organization, which has classes in sailing and windsurfing and rents 15-foot keelboats to experienced sailors. Paddling buffs can rent kayaks and SUPs here, too, or head to Paddle Boston, an outfitter that traces its roots back to 1973 and today has seven locations across Greater Boston.

Stay and Play

Landlubbers in search of fun should make tracks for the Boston HarborWalk, a 43-mile pathway that stretches from East Boston to Dorchester. It not only serves up great waterfront views but also connects to parks, beaches, museums, and shopping and dining spots. You could easily fill a whole day, in fact, with what you can discover in just a few miles.

With an eye toward America’s 250th birthday coming up in 2026, get a double dose of national history on the HarborWalk starting with Charlestown’s USS Constitution Museum, home to the world’s oldest commissioned warship still afloat. Follow that with a visit to the Seaport District’s Boston Tea Party Ships & Museum, which brings to life one of the most important events leading to the American Revolution (and where you, too, can heave some tea into Boston Harbor). Other must-see attractions along the HarborWalk include the New England Aquarium, the Boston Children’s Museum, and the Institute of Contemporary Art/Boston.

Prefer being outside to in? Soak up the sun at public beaches including South Boston’s Castle Island (where an ice cream cone from Sullivan’s is a time-honored tradition) and in green spaces such as Christopher Columbus Waterfront Park, located just a few blocks from the North End’s famed Italian pastries and restaurants. Or change up the scenery by detouring down one of the other notable paths that connect to the HarborWalk: the Charles River Esplanade, the Freedom Trail, and the Rose Kennedy Greenway.

Events, too, are a lively part of the Boston waterfront experience. Depending on when you visit, you might browse the fresh-caught/just-picked harvest at the new Fish & Farm Market, held Saturdays through October at the historic Boston Fish Pier; catch a concert under the tent at Leader Bank Pavilion; or join in a New Moon yoga experience at the Charlestown Navy Yard.

Kick Back and Relax

Like sailors returning home from the sea, visitors at the end of a long day’s adventure can breathe a sigh of relief at the sight of the Boston waterfront. Some of the city’s top bars and restaurants are perched alongside the harbor, with windows and terraces that maximize soothing water views.

Sitting on prime harborside real estate, hotels are favored hangouts for guests and non-guests alike. The Boston Harbor Hotel’s 60-foot archway on Rowes Wharf is a waterfront icon; past it lies the hotel’s Rowes Wharf Sea Grille and HarborWalk Terrace, home to the long-running Summer in the City concert series. Smaller and more tucked away but no less atmospheric is the seasonal outdoor bar at the InterContinental Boston, 510 on the Waterfront, overlooking Fort Point Channel. In the Seaport District, meanwhile, The Envoy Hotel ups the ante (as in, seven stories up) with its 6,000-square-foot rooftop bar and sprawling view of the city skyline.

Down by the water, dock-to-table dining is the rule. Among the seafood specialists serving the catch of the day within sight of the harbor is the locally based chain Legal Sea Foods: You’ll find its flagship in the Seaport District, Legal Harborside, a 20,000-square-foot, three-story eatery with head-on water views from bottom to top (hello, roof deck!). Another eye-catching seafood spot is The Barking Crab, a three-decade-old fixture set right on Fort Point Channel; its red-and-yellow striped tent is a magnet for outdoor dining fans. If fishy fare isn’t what you’re craving, there’s Italian (Venezia), Mexican (Temazcal), and laid-back pub grub (Joe’s Waterfront), to name a few—all with patio seating for maximum salt-air infusion.

And for the perfect nightcap? Consider heading across the harbor to East Boston to sip cocktails aboard The Tall Ship, an antique 245-foot charter boat reimagined as a seasonal floating bar. Reservations are recommended, as its popularity attests to the fact that when summer comes to Boston, there’s no better place to be than on the waterfront.