Best of Boston

2023 Best Family-Friendly Hike

Pleasure Bay Loop to Castle Island

There’s something for every kid on this flat 2-mile stroll: a beach walk, some exciting maritime hiking on a narrow jetty where waves crash along the rocks, and a real pre–Civil War fort. If that’s not enough to get the little explorers motivated, how about the promise of a cool dip in the bay or an even cooler raspberry-lime rickey from Sullivan’s when the hike is done?

South Boston,