A cultural guide to Key West

Key West sits at the farthest edge of America, literally and, some might say, figuratively. Straddling the Atlantic Ocean and Gulf of Mexico, the so-called Conch Republic has long been a haven for folks who march to their own drumbeat, from pirates and wreckers to Ernest Hemingway with his six-toed cats, and even today’s artists, musicians and renegades.

The island’s tolerant, easygoing ways have endured, so pack your flip-flops and an open mind as you escape for a Caribbean-like getaway where turquoise waters surround 19th-century forts, palm trees and colorful cottages line each block, resident roosters patrol the streets, and conch fritters with a side of key lime pie make a perfectly respectable dinner—or breakfast.  

Art & architecture

Conch-style cottages are a hallmark of Key West, with their cotton-candy colors, elaborate latticework and wraparound verandas, but you’ll also spot Spanish Colonial-style homes. Exhibit A: the Ernest Hemingway Home & Museum. Tour the estate where the Nobel Prize-winner drafted For Whom the Bell Tolls, and petted his six-toed cats—descendants of whom still roam the property’s lush gardens.

Meanwhile, the Museum of Art & History at the Custom House features a collection of 35,000 works, including several paintings by playwright Tennessee Williams. Next stop: The Mel Fisher Maritime Museum, founded by its namesake treasure hunter who in 1985 discovered a $450-million payload aboard a sunken 17th-century galleon just off Key West. Before setting out, get the lay of the land by exploring on a rented bike or take the hop-on-hop-off Old Town Trolley Tour. 

Food & drink

There’s no shame in heading to Jimmy Buffet’s Margaritaville for a cheeseburger in paradise, but if you prefer surf to turf, Conch Republic Seafood has you covered with conch fritters, blackened shrimp and other fresh catches. The lines are long but the food is worth it at Blue Heaven, a colorful, eclectic spot serving Floridian-Caribbean cuisine on its leafy patio; it was founded by a writer-artist couple and it shows (expect a wide range of art on display and free-roaming chickens). 

For a taste of the island’s Cuban influence, head to El Siboney Restaurant, where the bilingual staff have been dishing up roast pork, picadillo and other favorites since 1984. And save room for dessert at Kermit’s Key West Key Lime Shoppe, a local favorite that was once name-checked on Jeopardy!. 

Key West’s hard-partying tendencies go back centuries, so storied bars abound. There’s the casual but charming 1890 Green Parrot; Florida’s oldest bar, Captain Tony’s Saloon, once frequented by Tennessee Williams; the iconic Sloppy Joe’s, a celebrated former Hemingway haunt that now houses the island’s annual look-alike contest; and many more.  

Music

You can hear live music at just about any bar or restaurant on bustling Duval Street. But for something more refined, wander off the beaten path. Little Room Jazz Club, an intimate venue, offers straight-ahead jazz, cocktails named for music icons and Sunday Gospel brunch. For an evening that’s truly fierce, apply some flash lashes and catch the nightly drag show at the entertainment behemoth Aquaplex.

Of course, a trip to Key West wouldn’t be complete without experiencing the Sunset Celebration in Mallory Square, where crowds gather to watch tightrope walkers, fire eaters, buskers and other acts entertain for tips. During the last week of October, Fantasy Fest, a 10-day-long, bacchanalian street party takes over the city for a decidedly adults-only, Halloween-meets-Mardi Gras fete. 

Watch before you go

Key West is no stranger to the spotlight. It was the setting for the 1955 film The Rose Tattoo, based on Tennessee Williams’s play and winner of three Academy Awards. The Rose Tattoo House still stands at the corner of Pearl and Duncan streets. The Seven Mile Bridge had screen time in several movies, including the 1989 James Bond flick Licence to Kill and the 1994 Arnold Schwarzenegger blockbuster True Lies. And a trip to Key West is the perfect cure for a case of the Mondays, as the character Milton discovered in the final scene of 1999’s cult classic Office Space.