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LGBTQ Key West – A Gay Guy’s Weekend Guide to Key West

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.

Is Key West Going Straight?

In recent years, the once-bohemian enclave of Key West has undergone notable changes in its social landscape, prompting discussions about whether it remains as inherently gay-friendly as it once was. Historically recognized as a haven for the LGBTQ+ community, Key West has long celebrated its vibrant and diverse population. However, some argue that the island may have experienced a shift in its dynamic, moving away from the eccentric, queer, and “weird” reputation that defined it in the past.

While Key West may not exude the same level of countercultural flair it did in decades past, it undeniably remains a remarkably gay-friendly destination. The island’s commitment to inclusivity and acceptance persists, evident in its numerous LGBTQ+ events, establishments, and supportive community networks. Locals and visitors alike continue to embrace the ethos of diversity, fostering an environment where individuals of all sexual orientations feel welcome and celebrated.

Interestingly, the influx of straight visitors to Key West has played a role in shaping the island’s evolving narrative. The increasing presence of a broader demographic has sparked a heightened awareness of the island’s gay scene, prompting a cross-cultural exchange that enriches the overall experience.

While some may argue that Key West is not as explicitly gay, queer, or weird as it once was, the island’s enduring commitment to inclusivity ensures that it remains a microcosm of a gay haven. The fact that straight visitors are drawn to Key West not only indicates its broader appeal but also contributes to a more integrated and diverse community. The coexistence of different perspectives fosters understanding and challenges stereotypes, creating a unique atmosphere where people from all walks of life can come together and appreciate the richness of human diversity.

In essence, Key West may have evolved, but its core values of acceptance and celebration of individuality persist. The island’s ability to adapt and welcome a diverse range of people, both LGBTQ+ and straight, showcases its enduring commitment to being a place where everyone can feel at home.

In the end, Key West may not be as overtly eccentric as it once was, but its continued status as a gay-friendly destination reflects a broader societal shift towards acceptance and inclusivity.

LGBTQ Travel
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 except one state park and the popular Higgs Beach, 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.

holding sunscreen on fort zachary taylor historic state park

Where to Beach & Swim in Gay Key West

Key West, the southernmost point of the continental United States, is renowned for its pristine beaches and vibrant aquatic activities. For a quintessential beach experience, Fort Zachary Taylor State Park stands out as a top choice.

Nestled at the western tip of the island, this historic state park boasts a beautiful sandy shore with crystal-clear waters, making it an ideal spot for swimming and sunbathing. Beyond the beach, visitors can explore the well-preserved Civil War-era fort, adding a touch of history to their coastal retreat. There’s a small entrance fee you have to pay to enter the park and beach area, whether you park a car or not. It’s a great spot for sunset!

Higgs Beach is another gem along the shores of Key West, offering a laid-back atmosphere and a range of water activities. This beach is equipped with volleyball courts, picnic areas, and even a lovely pier for those seeking a leisurely stroll over the turquoise waters. The shallow and calm waters at Higgs Beach make it a family-friendly destination, while the adjacent Edward B. Knight Pier provides an excellent vantage point for breathtaking sunsets.

There’s a small beach bar and restaurant, Salute! On The Beach, which is a great spot to grab a drink. Personally, this is my favorite Key West beach but it’s a little further out and harder to get to.

gay selfie at the public pool in key west with palm trees and blue sky

For a unique and lively swimming experience, Dante’s Key West Pool Bar provides an alternative to the traditional beach setting. This vibrant establishment features a refreshing pool surrounded by lush tropical foliage, creating a relaxed oasis in the heart of Key West. Visitors can enjoy a refreshing dip in the pool, sip on tropical cocktails, and savor delicious bites in a lively atmosphere.

Dante’s is a very social place—and very loud! But it’s so convenient as it’s right in the main city center and the vibes are fun. Plus, it’s free to enter; you’re just expected to buy food or drink (don’t bring your own).

Whether you prefer the historical charm of Fort Zachary Taylor State Park, the family-friendly atmosphere of Higgs Beach, or the lively poolside experience at Dante’s Key West Pool Bar, Key West provides a diverse range of options for beach and swimming enthusiasts to bask in the sun and enjoy the island’s unique charm.

Where to Eat in Gay 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. I’ve been to A&B on every trip I’ve taken to Key West, actually—it’s the kind of place you go for a really nice meal. The perfect restaurant to treat yourself!

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 Island House in Key West stands as an iconic and inclusive retreat, epitomizing the laid-back charm of this vibrant island.

From its lively poolside events & parties to the tranquil ambiance of its lush gardens (which at night gives the feel of a gay sauna labyrinth), the Island House remains a haven for gay travelers seeking a comfortable and accepting environment, embodying the spirit of Key West’s enduring commitment to diversity and inclusivity.

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: One of my visits to Key West was supported and sponsored by the Florida Keys, though I’ve since been back on my own dime—most recently in 2023. 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.