1. Where to Stay
Find exclusivity on a secluded 27-acre island that’s home to Sunset Key Guest Cottages (from $495), a 40-cottage resort that’s just a five-minute ferry ride from Key West. If you’re traveling in a group, book one of the newer three- and four-bedroom colonial-style cottages with private pools. Book a Swedish massage (from $80) at the new spa, then decompress on your treatment suite’s individual patio.
Walk steps to the Gulf of Mexico at The Reach (from $179), the only property on Key West with a private natural-sand beach. Stay active by renting a variety of water-sports equipment (from $25) or attending morning yoga on the adjacent Casa Marina pier ($20), or lie back and enjoy poolside service from the hotel’s Strip House outpost.
Experience the island’s quirky side two miles away from historic Old Town at the fifties-era Ibis Bay Waterfront Resort (from $139), which was renovated and reopened last year. Enjoy the 600-foot stretch of sand (in the process of being extended) with jet-ski and kiteboard rentals (from $25 per hour) from the “fun” desk, or do something new and get a lesson in sand sculpture ($49 for two-and-a-half hours) from local artists Marianne van den Broek and Chris Guinto.
2. Where to Eat
Make a reservation in advance for the daily seven-course tasting menu ($75) at Fin, opened last year by chef Michael Schultz, a veteran of Philadelphia’s five-star Le Bec-Fin. Hidden away down a brick-paved alley, the restaurant serves artful French-Caribbean small plates with an emphasis on local seafood like spiny lobster and conch paired with unusual ingredients such as coconut, lychee, and kumquats.
Admire the salvaged décor and graffiti-tagged walls at 2¢ (416 Appleruth Ln.; 305-414-8626), where chef Chris Otten (formerly of the much-praised nine one five) has created an elevated gastropub menu that steers clear of middling Key West staples like conch fritters and Bud Light. Standout dishes include Thai chicken wings ($10) and yellowtail snapper with tarragon aioli ($24), and on weekdays there’s a pork-centric happy hour featuring free caramelized bacon from 4:30–6:30 p.m.
Skip the hour-wait for brunch with the cruise-ship crowd at Blue Heaven and eat across the street at La Crêperie, recently reopened in the Bahama Village neighborhood by two French natives. Chefs still make the spot’s signature buckwheat crêpes in familiar varieties, but there are now added specials like ratatouille-and-swiss ($11.25) and La Campagnarde, filled with frisée, lardons, tomatoes, potatoes, shallots, and an over-easy egg ($12).
3. What to Do
Take in the island’s famous sunsets on the water during a two-hour sail aboard the Classic Harbor Line’s new Schooner America 2.0 (November to April, $75 per person), a 105-foot sailboat modeled after the 1851 winner of the America’s Cup, which made its first trip in November. Grab a seat by the captain and ask about the treasure recently found off Key West as you sail out to Sand Key reef.
Skip the active but underwhelming art scene and instead head to the Key West Museum of Art & History ($7), currently hosting an exhibit celebrating the centennial of the 100-plus-mile Oversea Railway, which linked Key West to the Florida mainland for the first time. Other exhibits focus on the Spanish-American War, former resident Ernest Hemingway, and life on the island in the early twentieth century as depicted in a series of wooden reliefs.
Traverse the two-by-four-mile island by bike, especially if you’re staying in the historic Old Town, where it’s next to impossible to park a car. Eaton Bikes ($18 a day) delivers beach cruisers to hotels and offers roadside assistance if you have any troubles. Be sure to ride to the island’s best beach at Fort Zachary Taylor Historic State Park.
4. Insider’s Tip
Dry Tortugas National Park is a spectacular cluster of seven islands that sit 70 miles away from Key West, but the only practical way to get there is by booking a half-day flight with Key West Seaplane Adventures ($265 per person), the only charter plane company licensed to fly there. During the 40-minute flight, you’ll spot marine life, shipwrecks, and an active treasure site where half a billion dollars’ worth of loot has been found. Once you arrive, you can tour Civil War–era Fort Jefferson and snorkel in the reef.
5. Oddball Day
Take a break from relaxing and embark on an active, adrenaline-fueled day. Start with Lazy Dog’s Fit Fusion class (from $18), a one-hour aerobic core workout on the beach mixed with yoga and paddleboarding. Afterward, grab a café con leche ($2) at Amigos Tortilla Bar, along with a couple of the eleven varieties of tacos ($3–$4) served on homemade square corn tortillas. Next, make your way over to the Key West Bight by 3 p.m. for a two-hour class with Jet Pack Adventures ($249, book in advance), during which you’ll learn how to fly 30 feet above the water. Six years in development, this new aerial water activity debuted in Key West last summer. Afterward, stop by the Green Parrot, the oldest bar on the island, for a root-beer barrel shot (root-beer schnapps dropped in a highball glass of beer; $4.50) during the 5:30 “sound check” concert. For dinner, make your way to The Stoned Crab, where you can feast on a pound of stoned crab claws ($28), a local specialty, which the restaurant catches fresh daily on a dock just a few feet away from the kitchen. Follow dinner with sweets and innuendo at Better Than Sex, a red-walled dessert lounge that serves Between My Red Velvet Sheets Cheesecake ($12.69), which takes nine hours to make and won the local Master Chef competition for best dessert in 2011. Wind down the day in the Pink Triangle area at the longest-running drag show on the island at 801 Bourbon Bar. The two nightly cabaret shows (9 and 11 p.m.) feature a rotating roster of fifteen drag performers, but keep an eye out for Sushi, the house drag queen for sixteen years, who was a pioneer of Key West’s now-famous drag scene.
Find homes for rent, events calendars, and information on the local LGBT scene at Key West’s official site, maintained by the county tourism council.
Key West Attractions Association’s site is a hub for details on water sports, land and water tours, fishing charters, and more.
Brush up on local issues with the Key West Citizen, the local daily paper.
Ask for recommendations from locals on Key West News’s Facebook page.
Skip the party-town fixtures and take advantage of the island’s fixed-up resorts, serious-minded restaurants, and a growing selection of waterfront activities.