As the southernmost part of the Florida Keys, Key West has historically been a haven for dropouts of all stripes, from real pirates of the Caribbean to Prohibition rum runners and “Margaritaville” dwellers. Conchs, as the locals are called, cherish their outsider status, even briefly “seceding” from the country in the 1980s. In the past, the island’s main draw as the perfect weekend destination stemmed from the fact that it’s just a short flight from Miami yet far enough away from the mainstream, culturally speaking, for travelers to slip quickly into flip-flops and off the radar. Now, a spate of new hotels, restaurants and attractions is supplementing the classic call of Duval Street bars, Cuban-sandwich shops and sunset celebrations luring escapists to the island.
STAY: The new Ibis Bay Waterfront Resort remade a tired 1956 motel into a colorful party spot with a popular waterside restaurant and kitschy, affordable rooms. Stables of kayaks, Jet Skis, paddleboards, electric cars and scooters offer multiple ways to get around. The luxury-level Sunset Key Guest Cottages, reached by a private shuttle boat just off Mallory Square, recently opened a new spa cabana on the beach, bolstering its appeal as a romantic hideaway amid the revelry. Hilton Worldwide poured $43 million into upgrading the historic Casa Marina, A Waldorf Astoria Resort, which originally opened in 1920; it now boasts two swimming pools but still occupies one of the best swimming beaches on the island.
EAT: Popular chef Chris Otten recently opened 2¢ restaurant, which features gastropub fare (Pulp Fiction fans: There’s a Royale with Cheese), plenty of local seafood and free bacon served at happy hour. A newcomer to neighboring Stock Island, Roostica pizzeria fires Neapolitan pies in a wood-burning oven and serves family-style Sunday spaghetti dinners. Don’t miss the mahi-mahi or Korean beef tacos from Garbo’s Grill, a funky food truck that regularly sells out before its 5 p.m. closing time. Open around the clock, Sandy’s Cafe puts together the island’s best Cuban sandwiches and sends them out a streetside, quick-service window fronting the M&M Laundry.
DRINK: Sloppy Joe’s, along with its rival around the corner, Captain Tony’s Saloon, anchors party-hearty Duval Street, a magnet for the boisterous — local or transient. But beer snobs circle the Belgian and craft taps at The Porch, located in a mansion that’s rumored to be haunted.
DO: Papa — aka Ernest Hemingway — is back. For literature fans, he never went away, but for everyone else, recent movies like Midnight in Paris and HBO’s Hemingway & Gellhorn have revived the author who famously lived in an 1851 ship captain’s mansion on Key West for several pre-Cuba years. Among attractions at the Ernest Hemingway Home and Museum are dozens of polydactyl cats descended from his six-toed feline, Snowball. Sunset cues a nightly party — complete with tightrope walkers and unicyclists — down on Mallory Square, and during the day you can always take a Dancing Dolphin Spirits Charters trip to the middle-of-nowhere aquatic wild to view dolphins and visit pristine beaches on deserted isles.