Key West, Florida

Key West isn't just another port of call; it's a celebration of what makes a cruise experience unforgettable. Nestled closer to Havana than to mainland crowds, this island paradise delivers a signature mix of tropical beauty, intimate history, and a vibrant local culture that feels a world apart. On shore, you can trace literary and naval legends in the shadow of Ernest Hemingway's house or stroll Fort Zachary Taylor and the National Key deer refuge, then swap stories over conch fritters as the sun slides into the Gulf. Signature experiences run from snorkel and sunset sails to backcountry day trips and the otherworldly ferry ride out to Dry Tortugas National Park, where turquoise water and pristine reefs steal the show. The port's small-ship charm fuels a sense of discovery that larger destinations often miss, while a diverse fleet of visiting vessels—ranging from nimble expedition ships to midsize cruisers—find calm, shallow harbors and easy tendering. Back onboard, cruise lines fold Key West into immersive itineraries with locally inspired dining, onboard shore-excursion briefings, and island-centric enrichment that keeps guests coming back for more, long after they've left the Southernmost City.