4 Best Sights in South Boston, Boston

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We've compiled the best of the best in South Boston - browse our top choices for the top things to see or do during your stay.

Castle Island

South Boston Fodor's Choice

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.

John F. Kennedy Presidential Library and Museum

South Boston Fodor's Choice

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.

Castle Island Brewing Company

South Boston

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.

Recommended Fodor's Video

Edward M. Kennedy Institute for the United States Senate

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.

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