Key West Harbor Walk at the Historic Seaport

In the 19th and early 20th centuries, the Key West Bight was one of the most industrially productive harbors in the American South. Before synthetic sponges were invented, Key West sponge hookers harvested natural wool sponges from the Gulf flats, bringing millions of pounds across these timber docks for auction.

From the 1890s until the early 1970s, the Kraal docks held sea turtles harvested for canned green turtle soup, exported across the globe to luxury hotels. Today, that legacy is interpreted thoughtfully at the Key West Turtle Museum located along the Harbor Walk. In the 1950s, the discovery of massive pink shrimp beds off the Dry Tortugas created the 'Pink Gold' rush, packing the bight with over 500 working shrimp trawlers whose rigging filled the harbor horizon.

The Harbor Walk is a pedestrian-only timber and brick boardwalk that loops half a mile around the marina basin. As you walk past the slips, you can inspect majestic wooden tall ships such as the Schooner America 2.0 (a 105-foot modern replica of the 1851 America's Cup yacht) and classic Chesapeake bugeyes.

A favorite local spectacle happens along the cleaning tables behind the charter fishing slips near Grinnell Street: as fishing captains fillet their afternoon catch of mahi-mahi and grouper, giant Atlantic tarpon—measuring four to six feet long and weighing up to 150 pounds—gather right beneath the docks, churning the clear water as they feed on discarded baitfish.

The Historic Seaport is widely considered Key West's finest casual seafood enclave. Three waterfront institutions have anchored the bight for decades:

• Half Shell Raw Bar: Located inside an authentic 19th-century icehouse at 231 Margaret Street, famous for shucked raw oysters, steamed peel-and-eat shrimp, and communal wooden picnic tables.
• Conch Republic Seafood Company: Anchoring the center of the marina with a 100-foot wrap-around mahogany bar, serving Caribbean cracked conch, Key lime rum wings, and draft local beers.
• B.O.'s Fish Wagon: A quirky open-air driftwood shack at Caroline and William Streets, renowned for fried grouper sandwiches on fresh Cuban bread topped with key lime mayonnaise.