Key West Historic Seaport and Harborwalk

If Mallory Square is where Key West performs, the Historic Seaport is where it lives. This twenty-acre waterfront on the eastern edge of Old Town, still called the Bight by locals, was for most of its history a working harbor: sponge boats, shrimp trawlers, fishing smacks and, in the early twentieth century, turtling schooners that unloaded green sea turtles into pens for the cannery on the dock. The city bought the harbor in 1992 and turned it into a public seaport without sanding off the character, and today a harborwalk of about a mile runs along the water from the end of Front Street past marinas, historical markers, raw bars, dockside restaurants, boutiques and charter booths. It is free, open all hours, and one of the best walks on the island: tall-masted schooners tie up beside sport-fishing boats and the Dry Tortugas ferry, pelicans and tarpon wait for scraps at the fish-cleaning stations, and the old cannery and ice-house buildings now hold bars and restaurants with tables over the water. Many of Key West's boat trips leave from here — sunset sails, snorkel and reef trips, fishing charters, the Dry Tortugas ferry — so most visitors pass through at some point; the trick is to give it time on its own terms. Come in the late afternoon for a dockside drink as the schooners head out, or at night when the harborwalk is lit and the bars have live music. The honest caveats: the restaurants are not cheap, the busiest bars get loud, and the seaport is a ten-minute walk from Duval, which is a feature rather than a bug if you want a break from the crowds.

The history is posted along the walk. Key West Bight was the commercial heart of the island for generations — sponging boats from here supplied much of the American market in the nineteenth century, the shrimp fleet boomed after World War II when pink shrimp were found off the Dry Tortugas, and the turtle trade drew tourists to watch the catch unloaded until protections ended it. Markers along the harborwalk tell these stories, and several old industrial buildings survive, adapted into restaurants and shops. The schooners moored here, some of them historic and others built in classic style, keep the old maritime look alive and offer the island's most atmospheric sunset sails.

How to enjoy it: start at the Front Street end and walk east along the boardwalk, reading the markers and browsing the charter booths for tomorrow's trip; stop for conch fritters or oysters at one of the open-air raw bars; and stay through sunset, when the harbor fills with boats returning and the lights come on. Parking is limited and paid in the seaport lots, so walk, bike or take a hotel shuttle. The seaport hosts seasonal events, including a festive lighted-boat display around the holidays, and many of its bars have live music most evenings. If you are booked on the Dry Tortugas ferry or a morning snorkel trip, you will be here early — grab breakfast nearby and enjoy the quiet harbor before the day crowd arrives.

Who it suits: everyone. Couples love the sunset drinks and the lit-up evening walk, families like the boats, the fish and the pelicans, nightlife seekers have a lively alternative to Duval, and history fans can trace the island's maritime economy marker by marker. Pair it with a sunset sail or reef trip departing from the docks, with Duval Street a short walk west, or with the Mallory Square celebration if you would rather watch the sunset from land and come back to the seaport for dinner.