Blue Hills Summit & Harbor Islands Swim

The reservation's high point at 635 feet is reached via the Skyline Trail in a 3.5-mile circuit from the Hillside Street trailhead — the trail crosses open basalt ledge with unobstructed views of Boston's skyline, the Blue Hills pond complex, and on clear days, Mount Monadnock 70 miles north. The summit's Eliot Tower dates to 1877 and marks the highest point within 10 miles of any ocean on the US Atlantic coast.

A waterfront lobster shack steps from the Long Wharf ferry terminal, James Hook has been steaming lobsters and stuffing rolls since 1925. The ideal fuel-up before boarding the Harbor Express — order the classic lobster roll to go.

A 19th-century granite fort occupying the entirety of Georges Island, 7 miles offshore in Boston Harbor. Fort Warren held Confederate prisoners during the Civil War and has never been commercially developed — the lighthouse, cannon emplacements, and dungeon tunnels are accessible on foot. The ferry takes 40 minutes from Long Wharf; the island has a swimming beach on the harbor side.

A 62-acre undeveloped harbor island reachable by inter-island ferry from Georges Island — the closest thing to a wilderness beach experience within an hour of Boston. The ocean-facing shore has sand dunes, tide pools, and consistent surf; the inner harbor side is calm for swimming. World War II-era concrete gun batteries mark the island's military past.