Key West is a gay island mecca at the southern tip of Florida, famous for its relaxed, friendly and Bohemian atmosphere.
We loved it here so much that we stayed here for a large chunk of our road trip in Florida. There are so many things to do in Key West for gay travellers, along with a terrific gay scene. The majority of the gay bars and clubs of Key West are located in the same spot along the busy Duval Street, between Angela and Petronia Streets. There is a permanent Rainbow Crosswalk here so you can't miss it!
This is our gay guide to the best gay bars in Key West, along with dancing venues, drag show bars, beaches, events and best things to do. For accommodation options, be sure to check out our guide to the best gay resorts in Key West.
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Gay bars in Key West
These are the main gay bars in Key West to check out, including popular weekly parties:
- 801 Bourbon Bar: 801 is a large building standing proud next to the Rainbow Crosswalk. The bar is downstairs and upstairs is the club (see more below). The bar is a good place to come for a few cocktails to start the night. Also check out their Sunday karaoke nights between 4-8pm. 801 Bourbon is located at 801 Duval and is open everyday until 4am.
- Bourbon St. Pub: as you're making your way down the gay strip of Duval Street, you're most likely to be enticed inside by one of the speedo-clad Bourbon Boys standing outside. Bourbon St. Pub is located at 724 Duval Street, just across the road from 801 Bourbon Bar. Inside it's like a gay man's paradise, with pool bar area and sexy topless staff. They also have a dancing area, open everyday until around 4am.
- Aqua Back Bar: Aqua is a large complex with 2 bars and a dancing area. The front bar is called “Aqua”, which has drag shows, karaoke nights and Gay Bingo. The “Sidebar” is a club (see below) and the other bar is “Back Bar”, which is a more chilled place to just hang out. The entrance is just down Tabby Way on 711 Duval, and it is open daily until around 11pm.
- Bobby’s Monkey Bar: one of our favourite gay bars in Key West. Bobby's is a dive bar, like a gay Cheers, where everyone knows everyone. It's very homely with a pool table and so friendly. You'll quickly make a lot of friends, which is one of the reasons we love it so much. They have karaoke every evening from around 9:30pm, in which everyone gets involved (see video below). Bobby's is open everyday until 4am and is located at 900 Simonton.
- Saloon 1: male-only in-your-face leather bar…come in here and you're most likely see two guys butt naked making out on the main bar in front of everyone. One of their weekly highlights is the Friday evening “Cock Shock” contest. Saloon 1 is located right next door to 801 Bourbon at 504 Petronia Street, and is open every evening until 4am.
- Island House Pool Parties: Island House is a gay resort in Key West. On Wednesdays (5-8pm) and Sundays (12-4pm) they have clothing-optional pool parties. If like us you had one too many drinks on Saturday evening, coming here for brunch at their Sunday pool party is a great way to nurse that hangover! Island House is located at 1129 Fleming Street.
- La Te Da Sunday Tea Dance: takes places every Sunday between 4-6:30pm and includes cabaret acts. This is targeted more to an older crowd and people looking for an alternative to the Island House Sunday Pool party. La Te Da is located at 1125 Duval Street.
Gay clubs in Key West
The main gay clubs of Key West are based in the bars mentioned above, specifically at the following:
- 801 Bourbon: the upstairs is a club, which also has drag shows every evening. For us this was our favourite gay club in Key West. But if you go on a weekend, be warned it gets super busy! Watch our video below to get an idea of what a night out at the 801 Bourbon club is like! The club goes on until around 4am every day of the week.
- Bourbon St. Pub: has a club/dancing area which spills out into the outdoor pool area. Look out for their male-only “Bare It All” foam nights where no clothing is permitted!
- Aqua Sidebar Nightclub: dubs itself as “Key West's Best Nightclub”. When we went on a Saturday night it wasn't as busy as the other clubs, but this varies depending on which night you go. Sidebar also has quirky themed events such as the annual Thanksgiving “Turkey Testicle Festival”.
Drag shows in Key West
Key West is home to some of the best drag artists, like the hilarious America's Got Talent star, Randy Roberts and one of the Gaycities “Best of 2018 Hometown Queens”, Miss Sushi. These are some of the best drag shows in Key West to check out:
- The Crystal Room at La Te Da: The Crystal Room is La Te Da's Cabaret theatre, which has shows every evening. Our favourite is Randy Roberts, who was one of the funniest and most talented female impersonators we saw during our trip in Florida. Between his Cher and Bette Midler impersonations, he'll have you in a fit of giggles throughout the entire evening. Definitely one to get tickets for!
- 801 Bourbon: the “801Girls” perform at the upstairs bar of 801 Bourbon every evening from 9pm. 801 Bourbon is also where you're likely to see Miss Sushi performing.
- Bourbon St. Pub: they have drag shows for special occasions like Mardi Gras, the “Turkey TurnAbout” for Thanksgiving and “Shoe Drop” for New Years Eve, which features Miss Sushi.
- Aqua Key West: every evening from 7pm the “Aquanettes” perform to a seated audience. Saturday is the big night, which has 3 shows between 7pm and midnight.
Gay beaches in Key West
Although Key West doesn't have an “official” gay beach, these are the beaches you are most likely to find a large LGBTQ crowd:
- Higgs Beach: where the gay boys are most likely to head to. The water is usually shallow, which makes it ideal for swimming and snorkelling. Higgs beach is located at Atlantic Blvd between Reynolds Street and the White Street fishing pier.
- Smathers Beach: one of our favourite beaches in Key West because of the long sandy beach with shallow waters. It is located at the southern end of Key West near the airport, just off Roosevelt Blvd.
- Fort Zachary Taylor beach: named after Elizabeth Taylor who used to visit it a lot with her buddy Tennessee Williams in the 1950s. Unlike the other beaches, Fort Zachary Taylor is rocky, so remember to pack a pair of sandals. Fort Zachary beach is located at 601 Howard England Way.
Gay events and festivals in Key West
These are some of the best annual gay events in Key West you may want to plan your trip around:
- Key West Pride (June): the main Pride event in Key West, which usually takes place on the 2nd week in June. It also coincides with the finale of the “Stoli Vodka LGBT Bartender” competition, which also takes place in Key West during Pride week.
- Key West Tropical Heat (Aug): 4-day summer party event for men, which takes place in the 2nd week in August. It has different themed events, like pool parties, underwear party, fetish events and more.
- Womenfest Key West (Sept): the female equivalent of Tropical Heat and also one of the largest lesbian events in the world. This 4-day festival takes place during the 2nd week of September over the Labor Day weekend.
- Key West Headdress Ball (Oct): ticketed Cabaret event that takes place in October. It's part of the Key West Business Guild's annual fundraiser event. Due to its popularity it's usually a sell out, so buy your tickets early!
- Bear Weekend (Nov): takes places every November and includes foam parties, a “Butch Queen Bar Crawl”, a Bear Cruise and the “Mr Key West Bear” contest.
- Film Festival (Nov): ‘Passion Meets Paradise!' – the slogan of Key West's annual film festival, which takes place in mid-November. The event is huge and takes over the whole island – an event not to be missed!
Things to do in Key West
These are our some of the highlights and best things to do in Key West:
- Shopping on Duval Street: our favourite way to soak up the atmosphere of Key West is to take a stroll down Duval Street, checking out the many different boutique shops, galleries and souvenir shops. Some of the best gay shops to look out for along Duval Street include: InTouch, Graffitti and Leather Master.
- Sunset Cruise: this is a very popular activity in Key West and for good reason. The sunsets are stunning! One of the best ways to see them is onboard a cruise. There are many to choose from, but we highly recommend one of the more expensive ones, ideally on an elegant yacht like the Schooner America. The more expensive it is, the less crowded it is and better quality drinks and snacks – imagine champagne with fresh shrimps.
- Sunset Celebration at Mallory Square: this is a nightly arts festival at Mallory Square Dock, which starts around 2 hours before sunset. It's also one of our favourite spots to watch the sunset and the cruise ships coming in. There are arts/crafts exhibitors, street performers and food carts.
- Key West Butterfly & Nature Conservatory: another favourite of ours in Key West. This is a greenhouse-like garden with lots of pretty butterflies, some of which are massive. Filming a butterfly taking off is the perfect opportunity to try out the slow-mo setting on your phone's video camera!
- Tennessee Williams Museum: one of Key West's notorious gay residents was play writer Tennessee Williams. We strongly recommend visiting this fascinating museum, which is dedicated to his work and his life in Key West.
- Southernmost Point: Key West is kind of the most southernmost point of the US (the actual southernmost point is military land located further south). Despite this, there is a small monument you can visit. Be warned, there is usually a long queue for it!
- Ernest Hemingway Museum: the lavish house of the renowned writer is now a museum you can visit. Look out for the museum's resident (and very photogenic!) 6-toed polydactyly cats.
- Foodie tour: as foodies, we always strive to discover the culinary highlights of each place we visit. We tried the “Secret Food Tour“, which was a 3 hour journey from central Key West all the way to the Bahama Village with a local, who gave us a fascinating insight about the island's historic cuisine.
- Romantic dining: there are several excellent restaurants in Key West where you can go for a romantic meal and/or fine dining. One of the best is Latitude's Restaurant, located on its own private island. We also loved the Restaurant at LaTeDa, which has really good food and a hilarious charismatic Chef.
OUR FAVOURITE TRAVEL TIPS
⭐️ TRAVEL INSURANCE — We recommend you always take out travel insurance before your next vacation. What happens if you suffer from illness, injury, theft or a cancellation? With travel insurance, you can have peace of mind and not worry. We love World Nomads travel insurance and have been using it for years. Their comprehensive coverage is second to none and their online claims process is very user friendly.
⭐️ SAFETY & SECURITY — All travelers (gay or not) can sometimes encounter danger when traveling. CloseCircle is your “virtual body guard” mobile app which provides security alerts and support wherever you are in the world. They have a 24/7 emergency response team monitoring their users who will contact you immediately if the SOS swipe button is activated. Support can include anything from practical advice, to free evacuation from areas with extreme weather or security risks. You can read more about CloseCircle in our article about how to stay safe whilst traveling.
⭐️ ONLINE ANONYMITY — A VPN (Virtual Private Network) is a must in many countries: it allows you to surf anonymously and maintain your privacy whilst traveling. You'll particularly need it in countries where gay dating apps are blocked by the government. We recommend ExpressVPN, a reliable and cost effective service which we used and loved during our travels.
⭐️ HOTELS or APARTMENTS — When we plan a trip, we always look for the best hotel deals. We love Booking.com because not only do they have a comprehensive listing of accommodation options, they also offer the best prices. Added bonus: they provide 24/7 support and free cancellation for most listings.
⭐️ SIGHTSEEING and ADVENTURES — When we travel somewhere, we like to seek out the best experiences, whether it is cooking with locals in Bangkok, hiking on a glacier in Patagonia, or going on a wildlife safari in Sri Lanka. Our favorite place to look is GetYourGuide because they have over 30,000 highly rated activities, a user-friendly booking process with free cancellation and a 24 hour customer support.
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For more inspiration be sure to check out our gay guide to Florida Keys and also these articles from our big road trip in Florida:
- Tampa: read about our favourite things to do in Tampa and our guide to the gay scene of Tampa.
- Fort Lauderdale: for this super gay city we have a detailed gay travel guide as well as a guide to the best gay bars and clubs of Wilton Manors.
- Sarasota: check out our favourite romantic things to do in Sarasota as well as our Sarasota gay travel guide.