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Miles from Charlotte: 886

Flying time: 2 hours, 5 minutes

Nonstop service: American Airlines

The 2-by-4-mile island on the tail of the Florida Keys archipelago is a mashup of Bahamian, Cuban, and African American influences. Pastel, conch-style houses dot the narrow streets, where roosters have been free to roam since Key West banned cockfighting in the 1970s. Stroll through downtown—it’s a bit grittier than resort towns like Palm Beach or Seaside—and you’ll see restaurants and boutiques alongside cigar factories, rum distilleries, and dive bars frequented by famous residents like Ernest Hemingway and Tennessee Williams.

STAY

The Reach Key West is a beachfront retreat that’s tucked away from the bustle of Duval Street but still within walking distance of the restaurants and shops that line this main thoroughfare. The 150-room hotel has an outdoor pool, on-site seafood restaurant, and a rooster mural by Cuban American street artist DaveL that greets you on the patio. Most days, you can find the resort’s resident sand sculptor, Marianne van den Broek, creating 3D masterpieces on the beach, where she teaches sand-sculpting workshops. The Reach’s sister property next door, Casa Marina, has hosted celebrities and dignitaries since 1920. The 300-room resort is on the National Register of Historic Places and home to the island’s largest private beach. Amenities like the spa, fitness center, and adults-only pool are open to guests of both properties. Casa Marina will begin a six-month renovation in May, but the owners plan to open again for the holiday season.

The Reach Key West (above) underwent a multimillion-dollar renovation in 2019. “Gypsy Chicken,” a mural by Cuban American street artist DaveL, beside the hotel entrance. Below: Guides hip you to the town’s history during Barefoot Billy’s Jet Ski tours. Courtesy The Reach Key West, Curio Collection By Hilton; Barefoot Billy’s.

EAT

For a classic Key West breakfast (think seafood eggs Benedict and homemade banana bread), head to Blue Heaven, a blue-shuttered building in the historic Bahama Village neighborhood. Banana Café is a French bistro on Duval Street where you can get coffee, sangria, and sweet and savory crêpes. For a no-frills lunch or dinner, head to B.O.’s Fish Wagon, a driftwood shack that slings fried fish, conch fritters, burgers, and chicken sandwiches. The restaurant’s 80-year-old owner, Buddy Owen, began his operation out of a little wagon on Duval; today, his wife, Holly, still does all the cooking. If you explore the Key West Historic Seaport, stop by the White Tarpon Bar & Restaurant and treat yourself to a Key lime martini with a graham cracker-coated rim. Then head to Half Shell Raw Bar and feast on Key West pink shrimp and conch ceviche at picnic tables while you watch boats in the harbor. If you stay on-site, have a meal at Four Marlins, which is open for breakfast, lunch, and dinner. Enjoy bottomless mimosas, mahi-mahi tacos, and giant wedges of Key lime pie in the dining room or on the patio.

One of many cats that roam the Hemingway Home & Museum. Photo by Andy Newman/Florida Keys News Bureau.

PLAY

Book a Jet Ski tour at Barefoot Billy’s and circle the island on a Yamaha PWC with a guide who takes you on a 90-minute ride into the Gulf of Mexico and the Atlantic Ocean. Leave your phone and expensive sunglasses behind but be sure to bring cash to tip the guides, who jokingly call themselves “strippers of the sea.” At the Hemingway Home & Museum, visit the rooms and gardens where the Nobel Prize winner wrote classic works like Death in the Afternoon and For Whom the Bell Tolls. A colony of 57 cats, many of them six-toed, roam the property; according to tour guides, they descended from a sea captain’s feline given to the author. The Truman Little White House, which served as the naval station’s command headquarters during the Spanish-American War and World Wars I and II, was later the winter residence for President Truman. Hear stories from his 11 visits there and see the original man cave, where Truman’s custom poker table and bourbon bar stand frozen in time. When you need a sweet fix, visit the original Kermit’s Key West Key Lime Shoppe on Elizabeth Street. Pick up a Key lime pie (obviously) and stock up on essentials like Key lime candy, oils, seasonings, juice, salad dressing, and soaps. When you need an adult beverage, roll into Sloppy Joe’s, a local institution since 1933, named for “Sloppy” Joe Russell, who ran illegal speakeasies here.

The Duval Crawl: The Ultimate Key West Tradition

Duval Street, the 1.2-mile main drag that runs through downtown, is lined with 43 drinking establishments. Visitors and locals who hop from place to place often refer to this practice as the “Duval Crawl.” Stop by pubs, saloons, tiki bars, and frozen drink stands to sip local beers, rum runners, piña coladas, and Key lime martinis. Go on a self-guided route if you dare, or book a 2.5-hour guided tour through Duval Crawl. You’ll get five cocktails, a keepsake T-shirt, and countless memories (mishaps?) that can remain in Key West forever. 

TAYLOR BOWLER is the lifestyle editor.