4 Best Sights in South Boston, Boston

The library-museum is both a center for serious scholarship and a focus for Boston's nostalgia for her native son. The stark, white building (another modernist monument designed by I. M. Pei) at this Dorchester Bay–enclosed site 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 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 (currently under renovation). Two theaters show films about JFK's life. There's also a permanent display on the late Jacqueline Kennedy Onassis. The facility also includes a store and a small café.

Although it once was, Castle Island is no longer, well, an island. Today, this tip of South Boston is accessible by car and by foot from Day Boulevard. Castle Island's centerpiece is Fort Independence, built in 1801 (although there have been battlements on-site since 1644) and open for free tours on summer weekend afternoons. Castle Island is a popular spot for South Boston residents to walk their 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. If you get peckish, stop by Sullivan's (known locally as Sully's). Open February through November, come to this Castle Island institution of more than 60 years for a hot dog and fries. Views of the harbor and its outlying islands are expansive.

This taproom takes up an entire corner of the Cole Hersee Building. In nice weather, the garage windows in the front roll all the way up to reveal a contemporary rendezvous spot for craft beer lovers. Find signature brews, from IPAs to lagers, as well as some limited releases, on draft. Children are welcome if they're accompanied by adults.