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, and palm trees; that sums up life in 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 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%.
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 marriage has been legal in Florida since January 2015; what better place to combine a beach wedding with a tropical honeymoon?
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.
As Key West is such a small island, gay bars and restaurants can be found everywhere. However, you must go 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, there are no gay bathhouses or saunas in Key West. However, three of the gay-only resorts, have facilities that cater to those who enjoy these venues.
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