Editor's Note: Key West will re-open to visitors on Sunday, Oct. 1 and they need your support.
Only a 3-hour drive from Miami surrounded by clear turquoise waters of the Atlantic Ocean on the left and the Gulf of Mexico on the right (or faster still by plane), Key West is just as much the gay destination as it’s ever been.
Key West is close enough for the convenience of a staycation, but far enough away to feel like a real vacation. It’s the perfect weekend getaway for locals.
Once you arrive to the island and take a walk down Duval Street, you’ll see rainbow flags flying aplenty and gay couples soaking up the sunshine. To say nothing of when the sun goes down, the drag queens come out and you can get your fifth refill on that fruity cocktail to prepare for the nightlife that stretches into the early morning hours. There are the tried-and-true gay queer Key West favorites with a few new (or unfamiliar) spots worth adding to the itinerary for a quick getaway.
Key West has a long list of restaurants with seafood inspired menus, as the seafood here is as fresh as you will find anywhere, but there are many other choices of cuisine to satiate just about any craving. For Key West’s best dining options (and favorites among the gay locals), make reservations at Santiago’s Bodega (SantiagosBodeg.com), a Spanish-inspired Tapas bar with small plates sampling flavors from around the globe. Or a request a table for two at Michaels Restaurant (MichaelsKeyWest.com), one of the Keys’ top fine dining restaurants, for a more classic two- or three-course meal with a little island flavor. Wherever you go, be sure to save room for dessert - Key West is home base for Key lime pie.
With a nightlife that winds up at 4 a.m., the streets are alive all night. For Key West staples, visit the clothing-optional resort Island House or Aqua Bar & Nightclub (AquaKeyWest.com), which puts on a fabulous drag show—complete with Midwest tourists, of course—but fabulous nonetheless. For more of a low-key vibe, stop into Sidebar to grab a drink and chat with locals. Equator (EquatorResort.com), another clothing-optional resort, is worth dropping by for a drink and to enjoy the “scenery” (avoid buying a day pass here and at Island House by stopping in for a drink instead of a swim). For more local drag, 801 Bourbon Bar puts on a regular show in its upstairs cabaret bar. And for that backroom bar vibe, Saloon 1 is a shiny version of, well, what we know goes on in backroom bars.
There’s the safe tourist destinations of the Hemingway House, or even the Southernmost Point (be prepared to stand in line to snap an unobstructed selfie with the landmark), but being on warm crystal clear waters is hands down the best place to be in Key West. Sunset Watersports (SunsetWatersports.net) is the island’s top tour company for wave runner tours. Spend an hour and a half on the water following a guide on a 28-mile route around the island.
For history fanatics or nature enthusiasts, a hike at Key West’s Fort Zachary Taylor is a must—this state park is also a historic national landmark, built around a Civil War-era fort. It’s the perfect spot to catch the sunset on the beach. For those who are a little more fitness-minded, connect with Nomadic Stand Up Paddleboard (NomadicsUp.com), a highly rated gay-owned tour company taking guests out onto the water for guided eco and sunset stand up paddle boarding while exploring the serene natural beauty of the Keys. If you’re feeling especially in tune with nature, the guides even offer a paddle boarding tour in the buff. Just be sure you don’t forget the sunscreen!
Check into La Concha Hotel & Spa (laconchakeywest.com), located right on Duval Street in the middle of downtown Key West. In the middle of all the action, restaurants, shopping and many LGBT nightlife options, here guests can stay at this modernized take on classic Key West with maximum comfort. The Caribbean chic interior will immediately feel like a shady respite from the Florida sun. The 160-room hotel, built in 1926, played host to both Ernest Hemingway and Tennessee Williams, the latter as he was finishing his famous work A Streetcar Named Desire.
Book a suite resembling intimate studio apartments with coastal shutters, modern furnishings and ceilings painted in a deeply relaxing shade of blue to be sure to get the full “old Key West” experience and disconnect from the day-to-day. Indulge at the hotel’s Wine-O for happy hour with wines by the glass or the bottle, small bites, craft brews and flights of rum that will get you warmed up for a night out, or primed for dinner. 430 Duval Street, the hotel’s lounge-like restaurant, serves up fresh seafood and Carribean-inspired dishes.
Make time for a massage, pedicure, facial or body treatment at the hotel’s sixth floor Top Spa. Here you’ll get your treatment in your own private suite with floor-to-ceiling windows divulging a panoramic view high above Key West from downtown to the water. Each treatment is followed with a glass of your choice (the Prosecco is highly recommended paired with a long steamy shower in the spacious rain showers complete with its own panoramic view). Don’t hesitate to ask the hotel’s friendly and knowledgable concierge for itinerary ideas, or to help you book activities so you don’t miss out on the best of what the Keys have to offer.