Key West, Florida
There's a cheeky sense of fun across Key West, from the nightly sunset celebration at Mallory Square (keep an eye out for the acrobatic cats) to the colorful bungalows of Bahama Village. Add in mangrove reefs rich with marine life, museums with pirate treasure, and a great dining scene, and you have all the ingredients for a fantastic port call. Cruise ships dock near Mallory Square, within easy walking distance of the sights and sounds.
What We Love
Hemingway House: Ernest Hemingway lived and played in Key West on and off for much of his life. The writer lived here until 1940, and the art and furnishings include the desk where he finished "A Farewell to Arms."
Fort Zachary Taylor Historic State Park: Key West doesn't have much in the way of beaches, and the stretches are rockier than those on the Atlantic or Gulf shores. This state park is your best bet for sunning, swimming, and snorkeling.
Best Known For
Duval Street: See both sides of Key West's main drag. The northern end is lined with rowdy bars and restaurants, while the southern end is quieter, with wooden bungalows and the Mile 0 marker of U.S. Highway 1, America's oldest highway.
Key West Legal Rum Distillery: The Florida Keys were a bootlegger's haven during Prohibition, and this distillery uses that legacy for inspiration. Taste libations made from local sugar cane and infused with ingredients including tobacco, coconut, and Key lime.
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Who It's Best For
Partyers: This island is all about fun, and music pours from the bars until the wee hours. Bring your appetite for indulgence — and some aspirin for the next morning.
Water Lovers: The keys are a boater's sanctuary, and there are numerous ways to enjoy the sea, from kayak tours through the mangroves to sunset cruises.
Don't Say We Didn't Warn You
Bring an Open Mind: Key West is beloved for its "live and let live" bohemian lifestyle — just go with it.
Susan Moynihan is a Florida-based contributor to ShermansCruise who has also written for Parenting and Woman’s Day.