What's it really like?
Key West is the southernmost city in the continental United States, and it has a colorful gay history that dates back to the 1940s. It’s actually a tiny island, only 7.5 square miles, and it has always been a popular destination for gay travelers.
Think tropical weather year-round, white sandy beaches, palm trees and lots of men; that sums up life in Gay Key West.
Key West has a motto, ‘One Human Family,’ which means inclusivity for everyone. No matter your walk of life, you’re welcome with open arms in this county.
Gay people have and continue to hold high community positions in Key West; the recently retired police chief, Donie Lee, is openly gay. Key West currently has a gay mayor, Teri Johnston, who has held the office since 2018.
In the 1970s, because of its — at the time — hard to get to location, it was a safe haven for gay people to holiday, far away from prejudice and persecution. Hanns Ebensten, affectionately called the “Inventor of Gay Travel,” set up shop in Key West, and in 1972, he organized the very first official tour for gay men.
Today, you’re welcome everywhere, and the island is a must-visit destination for gay travelers.
Key West has you covered with whatever you’re looking for in the form of entertainment. From gay pool parties to drag shows or outdoor activities like gay fishing excursions, you’ll never be bored.
Pride festival is held in Key West every year in June. It’s a 5-day event culminating in the parade beginning at 5 pm on the Sunday afternoon.
Key West has year-round warm temperatures because of its ideal location close to the equator. Remember that it does have a hurricane season from June to November, so unless you’re a storm chaser, plan your holiday accordingly.
Getting there is easy; Key West International Airport is conveniently located on the island’s Southeast corner. It’s literally only a few minute’s drive into the heart of the city.
In gay Key West, the party never stops with five gay bars that have everything but a dull moment. Chill old-school, strut at a drag show, show off your smarts or vocals at trivia and karaoke nights, or get adventurous at a leather bar and naked pool parties.
Nestled in the Pink Triangle district, smack in the middle of Duval Street’s gayborhood, bar hopping is practically a competitive sport. Bars in Key West open early (Bourbon St. Pub starts the fun at 10 am) and go well into the night, most closing around 4 am.
Play.
Key West lacks saunas and cruise clubs, but who needs them? Cruise your way through gay Key West at two prime spots. Higgs is an unofficial gay beach and a stone’s throw from the Duval Street gayborhood. Another one is Smathers. It’s bigger, more isolated, and a hotspot in the high season.
Or just get a day pass for Island House Hotel. Clothing-optional, gay-only, and the pool parties? Legendary.
In the early 1970s, there were over 30 gay guest houses scattered around the island. Sadly, today, there are only four left. However, the rest of the hotels welcome the pink dollar.
It doesn’t matter which location you stay in, be it New Town or Bahama Village; there are hostels, hotels, and luxury resorts that cater to all tastes.
Similar to Honolulu, prices can be steep during high season because of the limited availability. If you feel like braving the low (hurricane) season, especially from September to November, prices can drop to as low as 50%.
Tours.
Discover Key West's enchanting mangroves with a unique guided kayak journey. Perfect for all skill levels, this eco-tour offers intimate encounters with local wildlife and serene waterways. Choose morning or afternoon departures, and yes, your furry friends are welcome too!
Jump on a Jet Ski and cruise 28 miles of Key West's stunning coastline. This 1.5-hour tour is the perfect way to explore the waters, with the option to ride tandem with a friend at no extra cost. Your guide will lead the way, ensuring a safe and wild adventure!
Get ready for an unforgettable food tour in Key West, where you'll explore off-the-beaten-path spots with your guide. Taste everything from seafood and Cuban bites to the iconic Key Lime Pie, all while learning about the city's rich history and architecture. The tastings make for a full lunch, so bring your appetite!
Hop aboard the custom-built SQUID catamaran for a small-group dolphin-watching adventure in Key West. After spotting these playful creatures, dive into the crystal-clear waters for an unforgettable snorkeling experience. With biologist-trained guides, you’ll get a deeper understanding of the marine life that calls these waters home.
Sail into Key West’s stunning sunset while enjoying live tunes from top local musicians. Sip on unlimited drinks—think wine, beer, margaritas, and sparkling champagne—and munch on appetizers as you relax and take in the view. It’s the perfect gay-friendly cruise to kick off your evening.
Enjoy a beach cruiser and glide through Key West's vibrant streets. This guided tour unveils the island's rich history and iconic spots like Mallory Square, Mile Marker Zero, and the Southernmost Point Buoy. Perfect for first-timers seeking a stylish introduction to the city.
Gays and the Law
Some counties in Florida state discriminate on account of sexual orientation and gender identity concerning private and public employment, housing, and public accommodations. Key West is one of the counties that does not discriminate.
Gay Key West marriage has been legal in Florida since January 2015; what better place to combine a beach wedding with a tropical honeymoon?
Getting Tested
There are many medical centers in Key West where you can get tested for HIV and other STIs if needed for around $50 a test. Alternatively, four places provide free STI testing.
You can choose between two providers if you need to refill your prep prescription while in Key West. Pep isn’t currently available in Key West, but there are numerous providers in the neighboring country of Dade.
Local Neighhorhoods
As Key West is such a small island, gay bars and restaurants can be found everywhere. However, in gay Key West, you must make a pilgrimage to the ‘Pink Triangle’ area on Duval Street for at least one night. You can’t miss it; rainbow-painted crosswalks mark it off.
Our favorite bar is the Bourbon Street Pub. It’s the home of ‘The Men of Bourbon,’ and there’s even a clothing optional, men-only pool. If you’re there over New Year, you’re in for a treat as Key West’s answer to the Times Square ball drop is the giant shoe drop at midnight.
801 Bourbon is another bar close by; it’s a Key West institution and has been serving gays for over 30 years. It’s kitschy with karaoke, bingo, and the most entertaining drag shows on the island.
If you’re looking for somewhere to eat, the gay-owned restaurant, Azur, is only a few steps from Duval Street and is Mediterranean-themed. It’s open from breakfast through dinner; brunch by the waterfall is our favorite reason to dine there.
American writer Ernest Hemingway lived in Key West in the 1930s, and his home is now a museum. For a touch of culture, be sure to include this on your itinerary.
Higgs Beach is the official gay beach, located on the very south of the island in the Casa Marina district.
Gay Weddings in Key West are big business, and with its incredible location, it’s no wonder. How’s this for a suggestion? Get married on a luxury yacht! The Schooner Appledore is the perfect choice.
Currently, in gay Key West, there are no gay bathhouses or saunas. However, three of the gay-only resorts, have facilities that cater to those who enjoy these venues.
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