Key West Historic Seaport is a working waterfront district in the Florida Keys, celebrated for its tall ships, fresh seafood, and deep maritime heritage.
Key West Historic Seaport occupies the northwestern waterfront of Key West and represents one of the last working waterfronts in the Florida Keys. The area has served as a hub for the local fishing and sponging industries for well over a century, and the weathered docks and low-slung warehouses still carry echoes of that commercial past. In the late twentieth century, the city undertook a careful restoration effort that preserved the district's maritime character while opening it to visitors.
Today the seaport is home to a mix of charter fishing boats, glass-bottom vessels, tall sailing schooners, and historic wooden ships. The two-masted schooner Western Union, a former cable-laying vessel that is now a Florida tall ship ambassador, is often moored here and available for day and sunset sails. Snorkeling and reef excursions depart regularly from the docks, making the seaport a natural starting point for exploring the coral reef system offshore.
The boardwalk that runs along the waterfront is lined with open-air restaurants and bars where the emphasis is on locally sourced seafood. Stone crab, yellowtail snapper, and spiny lobster appear on menus when in season, connecting the dining experience directly to the working boats visible just steps away.
Key West Historic Seaport offers a more grounded and authentic side of Key West than the busier tourist corridors nearby, giving visitors a genuine sense of the island's seafaring identity and the enduring rhythms of life on the water.
Visit during the early morning to watch the commercial fishing fleet return with their catch and see the docks at their most active.
Try a fresh stone crab claw or a bowl of conch chowder at one of the waterfront restaurants lining the seaport boardwalk.
Bring sunscreen and a light layer for afternoon boat tours, as the sun reflects intensely off the open water even on mild days.
Book a sunset sail aboard one of the tall schooners that depart from the seaport docks for some of the best views of Key West from the water.
Walk north along the boardwalk toward the Historic Seaport district to find locally owned shops and quieter spots away from the busier Duval Street crowds.
Sail to the Florida Keys Reef for guided snorkeling, lunch, and drinks
Snorkel two reef sites on a fast catamaran with drinks after the swim
Sail into Key West’s sunset with complimentary drinks on board
Explore Key West at your pace with an optional GPS audio tour
Sail, snorkel, and seek sandbars aboard a private catamaran
Sail a 1939 wooden schooner and take a turn at the helm
Private Key West harbor sail with time at the helm
Sail Key West aboard a 1939 wooden schooner with captain and crew
A private evening sail with quiet stargazing beyond Key West's lights
Sail Key West aboard a 1939 wooden schooner built for General George S. Patton
Toast Key West's sunset from a 45-foot catamaran with drinks included
Sail Key West’s historic waterfront aboard a hand-built 86-foot schooner
Cruise Key West’s waterfront with local history narrated by a licensed captain
Private catamaran celebration with bubbly, wines, and party platters
Chase big-game fish with a trip tailored to your skills and yacht comforts between bites
Watch Race World Offshore action from a premier spectator boat
Hoist sails and take the wheel aboard a 2-masted schooner