For most of the twentieth century this stretch of the South Boston waterfront was parking lots and warehouses. In a generation it became the Seaport: glass towers, plazas, restaurants, and a museum cantilevered over the harbor. Walking it costs nothing, the water is never out of view, and the contrast with brick-and-cobblestone Boston is half the fun.

Follow the Harborwalk

Start at Fort Point Channel, where downtown hands off to the Seaport across a set of short bridges and the Boston Tea Party Ships ride at anchor below. From there the Harborwalk — a public path that hugs the shoreline — threads the whole district past piers, boardwalks, lawns, and benches with front-row harbor traffic. The plazas along the way stay busy much of the year with markets, outdoor installations, and pop-ups; even on a cold day the walk itself is the attraction, and it never costs a dime. Keep an eye out for the working side of the port, too — fishing boats and the occasional towering cruise ship remind you this is still a harbor with a job.

The ICA, cantilevered over the water

The Institute of Contemporary Art is the district’s cultural anchor and its boldest piece of architecture — a glass box cantilevered out over the harbor, with a grandstand-style deck built for staring at the water. Inside are rotating exhibitions of contemporary art from around the world; outside, the building itself earns the trip. Admission is charged, with periodic free-admission windows — check their page before you go.

New Boston, best at night

This is Boston’s newest neighborhood, raised in a single generation on filled land and old piers, and it wears the contrast proudly: glass and steel where the rest of the city runs to brick. It is also a legitimate seafood destination, from casual counters to harborside dining rooms, with rooftop bars that put the skyline and the water in the same glass. Come for a late-afternoon walk, stay through dinner, and let the district do the thing it does best: glow.