SPONSORED — From the moment I landed in Key West, I knew it was going to be a good week. Arriving to the small island airport was just like I remembered from my childhood visits decades before. A small plane, walking on the tarmac, an airport with local art on the walls, and a single waiting area for luggage, taxis, and snacks. It’s hard to tell if you’re inside or out, except for the air-conditioning.
The warm, humid air on a late winter weekend was a welcome surprise. Warmer than I would have expected. On the way from the airport to my hotel, the windows down, a breeze through the window and palm trees overhead swaying in the wind. It felt like I’d landed in another world.
Key West has this mystifying effect. The subtropical climate, the warm & friendly locals, the quiet nights abuzz with laughter and love. Tennessee Williams wrote about Key West, “I can write anywhere, but I write the best here.” Something in the spirit of Key West just makes it that kind of perfectly livable, perfectly enjoyable destination.
Maybe that’s what has attracted LGBTQ travelers to Key West for decades. It was in the 1970s when many gay men and lesbians started to flock to the city, attracted by the climate, the creative community of locals, and an accepting and open atmosphere. Today, that carefree attitude toward life is still there. The number of attractions and things to do are endless; it’s easy to lose track of time when in Key West.
Gay Guide to Key West
What to do in Key West
As the southernmost point in the continental USA, and an island of just four square miles, Key West has a surprising amount of things to see and do. While there aren’t many sandy beaches, there’s still plenty of sunshine and swimming pools. Of course, with the subtropical climate in Key West, the best activities are outside—and many are in the water!
Fury Water Adventures offers a variety of high-adrenaline water activities and sports. Some of their more popular options include full-day excursions for parasailing, jet skiing, kayaking, and snorkeling. Their Reef & ‘Ritas Snorkeling adventure is a half-day tour that goes out to the Florida Reef (also called the Great Florida Reef) and includes unlimited margaritas!
Back on land, though, there are still plenty of activities. The Key West Butterfly & Nature Conservatory offers an inviting environment filled with hundreds of beautiful butterflies, birds (flamingoes!), and flowers—a perfect little escape from the sun, with a well-stocked gift shop for souvenir shopping, too.
In a city made popular from its many famous past residents, there’s a lot of history in Key West to explore. Tennessee Williams, a gay literary icon, called Key West home and the Tennessee Williams Museum offers a self-guided tour through his life and work. Learn about his life and work and an introduction into Key West’s literary history with letters, artifacts, and memorabilia from his time in Key West.
However, the most popular historical home in Key West is the Ernest Hemingway Home & Museum. Hemingway lived and wrote in Key West for nearly 10 years, and his former home is a monument to his life and work while on the island. On the property, you’ll find Key West’s first swimming pool and a flourishing colony of cats—most of them, strangely, with six toes! It’s worth wandering the grounds and taking a guided tour to learn more about Hemingway’s history in Key West.
For up-to-date and local listings of things to do in Key West, especially for LGBTQ travelers, the Gay Key West Visitors Center on Duval Street has lots of useful tourist information. Their directory of gay friendly Key West businesses includes discount coupons, and the staff inside are great for making recommendations on the best activities, restaurants, and nightlife. The visitors center is operated by the Key West Business Guild which has promoted the island to LGBTQ travelers since 1978.
Where to Eat in Key West
Key West is an entertainment destination as much as it is a foodie destination. The two-by-four-mile island has a lot of seafood, predictably. For seafood, don’t miss the local specialty of conch fritters from The Conch Shack. The conch meat is fried in a tasty ball with spices and served with a dipping sauce. A perfect happy hour snack! (And The Conch Shack has some of the best beer and alcohol prices for any other bar in Old Town Key West!)
For fine-dining seafood, Azur Restaurant (gay-owned) serves Mediterranean-style dishes infused with traditional Italian ingredients. At the A&B Lobster House, you can enjoy sunset over the harbor from their outdoor, wrap-around patio. Serving traditional surf & turf dishes, it’s the perfect spot for a romantic dinner.
While seafood is available just about everywhere in Key West, there are plenty of other options, too. Like all gay destinations, brunch is big! Blue Heaven serves a heavenly homemade banana bread and a decadent lobster eggs benedict in a beautiful courtyard with roaming chickens. The food is some of the best on the island, and the live entertainment is quirky and fun in a way you can only expect from Key West.
Most of the Key West hotels and resorts also have on-site restaurants. The gay, clothing-optional resort Island House offers a surprisingly tasty lunch and dinner menu for guests and visitors, with fresh seafood and snacks served poolside. The views are great, but so is the food. And a regular happy hour makes it a fun evening hangout, too.
La Te Da (also a gay-owned hotel) has a sophisticated restaurant and hotel right on Duval Street, Key West’s gay neighborhood. The restaurant serves fine dining with seasonal specialties and offers live entertainment most nights in an outdoor setting. Bagatelle is a seafood-focused restaurant in the heart of Key West’s entertainment district. With a wraparound balcony perfect for people-watching, the casual but sophisticated restaurant serves seafood and classic American eats in a converted 19th century home.
In a town with as much life and energy as Key West has, don’t miss out on desert! So many restaurants and cafés lay claim to the best Key Lime Pie, but stop into Kermit’s Key West Lime Shoppe for a whole range of Key Lime-flavored deserts and foods—everything from salsas to candies, and even an ice cream version.
Where to Drink and Party in Key West
The nights in Key West are long, and they should all start at sunset with the daily Sunset Celebration at Mallory Square. It’s a nightly street carnival with arts and craft vendors, street performers, food stalls, buskers, and musicians all crowding around the harbor to watch the sun disappear behind the horizon. It’s full of energy and life—a classic example of that Key West vibe you won’t find anywhere else.
All of Key West’s gay and lesbian nightlife takes place on Duval Street, in an area called the Pink Triangle. The Pink Triangle gayborhood includes a cluster of LGBT bars, entertainment clubs, and even a rainbow crosswalk. Drag shows happen every night at Aqua Nightclub, while Sidebar, 801 Bourbon Bar, and the Bourbon Street Pub, and even La Te Da Cabaret Bar occasionally host special shows and performances.
All the Key West gay bars offer happy hours and the casual, carefree environment of the island life makes it easy to meet and mingle with locals. Look out for visiting performers at some of the entertainment venues and theaters. The best source of information is Q Magazine—the only monthly guide to gay Key West. You’ll find copies in most of the gay shops, hotels, and bars around the island.
Where to Stay in Key West
In Key West, many guesthouses cater primarily to gay men, lesbians or a combination of the two. They’re often private hideaways tucked underneath swaying palms, furnished with island wicker, rattan, and the expected bric-a-brac. In fact, there are four different LGBTQ-specific, clothing-optional resorts.
Island House Key West is one of the most popular. It’s undergone several redesigns and updates, and the private, secluded space attracts visitors from all over the world. With a world-class gym and a 24-hour poolside bar & café, the clothing-optional resort offers a great escape.
The sun deck and pool are popular all times of the day and night, and the rooms are all surprisingly spacious with plenty of on-site amenities. It’s the type of place where you don’t really want to leave during the day, because the pool’s so comfortable and there’s plenty to see while on the property.
For a design-centric hotel option, The Marker resort is located steps from the Key West harbor and has three pools on-site, including an adults-only one. It’s the newest hotel built in Old Town and the rooms are beautifully designed with simple tastes of luxury.
The Marker hotel & resort is most convenient if you’re planning to see a lot of the sites and spend your days shopping along Duval Street or in the souvenir shops of Old Town Key West.
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Key West is a unique gay destination—different from other LGBTQ hotspots and beach towns across the United States. In its own special way, there’s a fun and funky atmosphere—a bit like other small beach towns, but special in its own ways. With a large LGBTQ local population and a history of support for the community, it’s one of America’s best LGBTQ destinations.
Note: My visit to Key West was supported and sponsored by the Florida Keys. Discover more travel tips for the Florida Keys on their tourism website. Additional LGBTQ tips and a guide to the town is produced by the Key West Business Guild.