19 Best Sights in The Seaport, South Boston, and East Boston, Boston

You know you'll have found the country's second-oldest children's museum when you find the giant Hood milk bottle structure. This museum has always been ahead of the curve with creative hands-on exhibits, cultural diversity, and problem-solving. Some of the most popular stops are also the simplest, like the bubble-making machinery and the two-story climbing maze. At the Japanese House, you're invited to take off your shoes and step inside a Kyoto silk merchant's home. Children can dig, climb, and build at the Construction Zone. In the toddler PlaySpace, children under three can run free in a safe environment. There's also a full schedule of special exhibits, festivals, and performances, and Children's Wharf out front is a beautiful place to walk or rest.

Stretching for 43 continuous miles, Boston Harborwalk is a walking trail that skirts the twists and turns of the coast from Charlestown down to the city of Quincy. In the Seaport District specifically, the Harborwalk journeys along Fort Point Channel, around Fan Pier, up Seaport Boulevard, and out and around the Black Falcon Cruise Terminal. Along the way, pedestrians can see art exhibits, stationary viewfinders, open green spaces, and incredible Boston Harbor views. Marked signs point the way, and maps can be found online.

Although it once was, Castle Island is no longer, well, an island. Capping the South Boston neighborhood, Castle Island is accessible by car and by foot from Day Boulevard. Its centerpiece is Fort Independence, built in 1801 (although there have been battlements on-site since 1644), open for free tours on summer weekend afternoons. Castle Island is a popular spot to walk dogs, jog, or cycle, whether just around the island itself or along the water-set Pleasure Bay Loop. There's also a nice playground for kids. Stop by Castle Island institution Sullivan's for a hot dog, fried seafood dinner, or ice cream. Views of the harbor and its outlying islands are expansive.

Harpoon Brewery holds Massachusetts's first-ever brewing permit, obtained in 1986 by three college friends who wanted to create a fresh beer culture in their hometown. Today, Harpoon's Boston brewery features 25-minute guided tours and tastings for beer lovers from around the globe. Harpoon's on-site beer hall pours a rotating lineup of limited-edition and pilot beers, non-brand beers, and ciders—try a flight of UFOs or Clown Shoes. It also serves handmade pretzels and pizza.

It's hard to say what's more cutting-edge: the Institute of Contemporary Art/Boston's cantilevered building or the works that reside within. The events calendar is studded with changing, thematic exhibitions by the contemporary art world's brightest talents. Visitors will also see some curated pieces from the ICA's permanent collection, including some by Robert Mapplethorpe, Yayoi Kusama, and Louise Bourgeois. Live programming, from film festivals to talks to outdoor concerts, take place regularly. Don't miss the ICA Store on the ground level, where you can pick up an inventive trinket of your own.

Sitting at the edge of Dorchester Bay, this stark, white building (a modernist monument designed by I. M. Pei) pays homage to the life and presidency of John F. Kennedy, as well as to members of his family, including his wife, Jacqueline, and brother Robert. The library-museum is both a center for serious scholarship and a focus for Boston's nostalgia for her native son. 

The library is the official repository of JFK's presidential papers and displays re-creations of his desk in the Oval Office and of the television studio in which he debated Richard Nixon in the 1960 election. Permanent exhibits focus on his life before politics, the 1960 presidential election, the Peace Corps, and the U.S. space program. There's also a permanent display on the late Jacqueline Kennedy Onassis. The facility also includes a store and a small café.

Stop, rest awhile, and have some fun. That's the purpose of The Lawn on D, a free-to-all open green space that features a plethora of games like bocce, corn hole, Ping-Pong, and pickleball, and chairs for lounging. In warmer weather, you can often catch a live concert or film screening here, or a public art installation. A concession stand makes sure visitors are well fed. The only catch? You can't bring Fido.

This 300-acre patch of remaining wetland environment is indicative of the salt marsh landscape that covered Boston when early settlers arrived and which today has been filled in. As you walk or run Belle Isle's gravel paths, listen to the sound of the marsh's diverse bird community, which includes the American kestrel, belted kingfisher, great blue heron, northern harrier, and salt marsh sparrow. Boardwalks venture into the marsh for great viewing and photo ops.

Surrounded by water on three sides, Black Falcon Pier is a stop on Boston's Harborwalk that seekers of amazing views won't want to miss. There's not much to do out this way at the end of the Seaport District except gaze at the fishing vessels, barges, and cruise ships navigating the inner harbor. However, lots of visitors find themselves out this way as Black Falcon Pier is home to Flynn Cruiseport Boston, where major cruise ships dock daily with Boston as a port of call.

Occupying an entire corner of the Cole Hersee Building, this taproom has signature brews, from IPAs to lagers, as well as some limited releases, on draft. In nice weather, the front garage doors open to reveal a contemporary rendezvous spot for craft beer lovers. Children are welcome if they're accompanied by adults, but it's 21 and over after 8 pm. Check the website for frequent public events, including weekly trivia on Tuesday.

You've got to really look for the garage doors that mark the entrance to this zero-frills local taproom. Once you make it inside the industrial space, you can sample flights of Downeast's fresh, unfiltered cider varieties—many of which are only available at the cider house. While many breweries these days welcome the whole family, this isn't one of those places. Of course kids are allowed, but they must remain seated and Downeast does not serve any food.  There's limited seating and no standing room so you may have to wait for a table.

Located adjacent to the JFK Library and Museum, the Edward M. Kennedy Institute for the United States Senate offers another view of the workings of the U.S. government, this one through the lens of the Senate and one of its most influential members. Interactive exhibits take visitors through a day in the life of a senator, and the highlight is the stunning full-scale representation of the Senate Chamber. In addition, there’s an exact reproduction of Senator Kennedy’s office, complete with photos of his family, model ships, and letters from his mother. It's definitely worth planning to visit both Kennedy attractions.

This historic district, which was designated by the City of Boston in 2009, features the city's largest, most cohesive grouping of late-19th- and early-20th-century industrial loft buildings. The Boston Wharf Company owned and developed the area from 1836 to 1882. Today, the small, walkable, revitalized area sits between the Fort Point Channel and the Seaport District and is home to working artist studios, bars and restaurants, and some small businesses.

Whimsical murals on cement barriers, colorful wooden chairs mounted on the outside wall of a commercial building, large-scale sculpture—together around 30 pieces generate an artistic ambience in the industrial setting of East Boston's working marina and shipyard. HarborArts curates a rotating collection of works by local and international artists across 14 acres, completely open to the public for perusal.

The Institute of Contemporary Art/Boston's seasonal outpost first opened in 2018 after renovations to a dilapidated former copper-pipe facility in East Boston's working shipyard and marina. Every summer, a single large-scale, immersive art installation makes the 15,000-square-foot space its own. A smaller gallery delves into the shipyard's history.

Believe it or not, the public is welcomed in for a visit to this architectural wonder and federal house of justice. Galleries across the courthouse feature rotating exhibitions on a variety of themes, from maritime history to the judicial system. Don't miss Ellsworth Kelly's permanent installation The Boston Panels in the courthouse's rotunda. It's not uncommon to see a tall ship or a charter vessel docked outside, in season. Book a free tour through the website.

A 35-foot golden and green statue of the Virgin Mary standing atop a globe dominates the Pope Paul VI Pilgrim Plaza that welcomes curious visitors and religious pilgrims to this Roman Catholic shrine. From its perch in Orient Heights, the shrine also boasts some pretty spectacular views of Logan Airport and the downtown skyline. Beneath the plaza, a sprawling sanctuary offers a quiet retreat, and some holy relics are on display. Masses are offered weekly in English, Spanish, and Portuguese.

Opened in late 2024, this whimsical entrée into the Seaport District has locals and visitors alike licking their lips. Check out 14 immersive, interactive exhibitions across two floors inspired by the eponymous dessert, including a sprinkle pool, a carnival, and the Hall of Freezers. It should go without saying that there are samples of the real thing—as many as you can eat, in fact.

Sandwiched between Marginal Street and Boston Harbor, the gorgeous, 6½-acre waterfront Piers Park features a grassy, green retreat from urban life and sweeping views of downtown Boston to the southwest. It is so named because of its many long piers that jut into the inner harbor. For a bit of historical knowledge: it's also in close proximity to the site where naval architect Donald McKay built his reputedly fast clipper ships. Take a stroll down the promenade and let the kiddos enjoy the large playground.