At the southernmost end of the coral cay archipelago known as the Florida Keys lies Key West, a tropical island that embodies the spirit of what it means to have a freewheeling vacation.

The lush island’s laid-back persona is certainly key to its fame, but there’s more to see and do in Key West than watch the sunset in Mallory Square and relax a with a cold drink at Sloppy Joe’s, one of Ernest Hemingway’s favorite haunts (though both of these stops are worthy of anyone’s bucket list).

Literary Local
If you’re looking to leave the hot spots to the tourists and do Key West like a local, start by exploring another famous writer’s Key West roots. Housed in a charming yellow island-style home, the Tennessee Williams Key West Exhibit is a museum dedicated to the legacy of one of the foremost 20th-century playwrights.

Explore the largest collection of Williams’ memorabilia, including first-edition plays and books (Williams authored such famous works as A Streetcar Named Desire and Cat on a Hot Tin Roof). There’s even a typewriter used by the author during his time in Key West from 1941 until his death in 1983.

Island Immersion
The Tennessee Williams Museum is part of the Key West Historical Society, which works to preserve the history and culture of Key West. Three other must-see historic sites also fall under its purview: The stately Custom House towering over Mallory Square, the Lighthouse Tower & Keeper’s Quarters and Fort East Martello, a Civil War fort and tower.

Built in 1891 and situated next to the Naval Base, the Custom House was once the hub of Key West, housing its postal service and district courts. Peruse the historical exhibitions displayed inside as well the building’s extraordinary exterior – this architectural marvel is an excellent example of Richardsonian Romanesque architecture.

For a different “view” of Key West, climb the 88 steps at the Lighthouse Tower & Keeper’s Museum for breathtaking 360-degree vistas. Built in 1848, it was one of few lighthouses to open with a woman as keeper. Today, it’s a living museum of the island’s maritime heritage.

History buffs will also love Fort East Martello, where you can see relics from the Civil War and learn about the island’s history of cigar making and wrecking, the term used to describe the rush to dive wrecks to claim their salvage.

Getting Around Key West
Both the Custom House and the Lighthouse Tower & Keeper’s Museum are found along the route of the famous Conch Tour Train or within walking distance of one of its stops. This 90-minute tour is a great introduction to the island for first-timers and an easy way to access multiple landmarks in one day. Whether you keep up with your tour guide for the entire tour or you hop on and off at multiple stops throughout the day and explore on your own, it’s hard to imagine a visit to Key West without riding (or spotting) an open-air conch train.

Wherever you go in Key West – whether you’re strolling past the shops along Duval Street, snapping selfies at the Southernmost Point, or setting off on an unmarked footpath shaded by lush bougainvillea – there’s no shortage of surprises to be found in the Conch Republic.

Enjoy the fun and sun of Key West and book a stay at a Hilton.

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