Castle Island & Fort Independence

Castle Island is the quintessential Boston family outing, and it's been that way for generations. Located at the tip of South Boston, this peninsula (connected to the mainland by a causeway since the 1930s) combines a Revolutionary War-era fort, a sheltered beach, a waterfront walking loop, and one of Boston's most beloved snack bars into a perfect free day out.

Fort Independence is the centerpiece. The current structure is a granite star fort built in 1851, but fortifications have stood on this site since 1634, making it one of the oldest continuously fortified sites in the United States. Kids can explore the fort's exterior, walk the ramparts, and imagine defending Boston Harbor.

Free ranger-led tours on summer weekends add historical context and Edgar Allan Poe lore (Poe was stationed here as a young soldier, and the fort allegedly inspired 'The Cask of Amontillado').

The walking loop around Castle Island and Pleasure Bay is approximately 2 miles on a flat, paved path. It's one of the best stroller/bike/scooter routes in the city — flat, scenic, and ending right back where you started. The views include Boston Harbor, Logan Airport (kids love watching planes land), and the harbor islands.

Pleasure Bay beach is the swimming spot. Protected by the Sugar Bowl causeway, the water is calmer and warmer than open-ocean beaches — ideal for young swimmers. On summer weekends, the beach is packed with South Boston families who've been coming here for decades.

Sullivan's snack bar completes the experience. Open since 1951 (seasonal, roughly March through November), it serves hot dogs, fried clams, lobster rolls, and ice cream from a walk-up window. The prices are fair, the portions are generous, and eating a hot dog on the seawall watching planes land across the harbor is one of those simple pleasures that makes you understand why Bostonians love this city.