Key West in Florida is home to the most southerly point in America. It's one of the world's favourite gay retreats, especially among travellers looking to spend a week or two at a self-contained, gay-exclusive resort, writes OutUK correspondent Adrian Gillan.

Key West showing Mallory Square

Key West is the US mainland’s southernmost point, and the westernmost pearl in a string of islands that starts curling out down towards Cuba at Key Largo - itself just forty miles below Miami. There’s only one road, skimming across the water between an Ocean and a Gulf and it ends here: in a blossom-covered village brimming with whitewashed Victorian homes, set off against a warm, clear turquoise sea.

Just two by four miles in size, if you don’t cycle around Key West, you walk - about the Old Town and Fleming Street where many of the gay guest houses are, or along Duval Street, the island’s queer heart; and if you’re not walking you’re probably just lying down on some shady lounger or porch swing, basking on a jetty or by a secluded hotel courtyard pool, or simply watching the setting sun from Mallory Square. Most of the gay quarter occupies vintage buildings in a quaint historic district.
Photo courtesy Key West Business Guild.


Friendly and fast-expanding, the Key West Bear Weekend happens every November. This year amongst the attractions are Woof! Bear Soup Party when you can grab a swimsuit (or not!) and meet friends. Bourbon Bar's World Famous Cabaret Drag Show and The Leather Master Shopping Experience which includes an open bar and clothing optional shopping. The Gay Trolley Tour of Key West and then Key West Bear Weekend's Main Event - FURBALL. There's also the Bear Ass Tea which is a frisky clothing-optional shindig and then the La-te-da Bar World Famous Tea Dance with a cock...tail and a twirl!

You might also check out the annual Fantasy Fest, in mid to late October, which attracts flocks of gays down along The Keys to its parties and camp celeb look-alike comps, climaxing in a parade on the last Saturday. There's also a chance to have your body painted, enjoy a Royal Coronation or Zombie Bike Ride or take part in a Kinky Carnival when you can only get in with a Kinky Costume!

Twice a year in July and late November there's no need to dress up to try the no-clothes Bone Island Bare It All. It's a way to gather gay naturists for a weekend of camaraderie and share with them the beauty and fun of Key West. And, of course, don't forget Key West Pride, the first of those celebrations at the beginning of June. Whether you're looking to party with friends, travel with family, or get lost in the magic of our tropical island, you can rediscover Key West and discover how one island's One Human Family philosophy has created one of the most integrated and unique communities in the world.

For this next year, here's the line-up of events:

  • Key West Pride is held at the begining of June and the next is from June 5th - 9th 2024
  • Bone Island Bare It All is July 5th - 9th 2023 and also from November 30th - December 3rd 2023
  • Fantasy Fest is in October from Friday Oct 20th - Sunday Oct 29th 2023
  • Key West Bear Weekend is from November 1st - 5th 2023


The town’s numerous gay-run guesthouses are mainly in vintage buildings in the quaint historic district near the gay area, many men-only - often clothing optional. Private hideaways hidden beneath swaying palms, furnished with wicker armchairs and antiques, many also have their own private pools - perfect for gangs of gay gaggles.

Key West is one of the world's favourite gay retreats.
Photo courtesy Key West Business Guild.
The alpha-and-omega of gay Key West all-male lodgings, Island House on Fleming Street boasts a loyal following, some of whom scarce venture off-site - instead bathing nude, dining poolside, pumping iron in the gym and pumping other things in the infamous in-house spa and red light zone. Great-value day-passes available for non-resident guests.

Alternatively Alexander's in the same street not far away is a slightly smaller, but very classy, compound in an idyllic setting.

New Orleans House can be found among the bars and eateries of Duval Street 2 blocks from Highway 1. This lively gay adults-only guesthouse is 4 minutes' walk from the Ernest Hemingway Home and Museum, and an 11-minute walk from South Beach. The 11 unfussy rooms have free Wi-Fi and cable TV, as well as minifridges, microwaves and coffeemakers; some offer kitchenettes and/or balconies. A 1-bedroom apartment and a cottage provide pull-out sofas. Freebies include happy-hour drinks, entry into partner nightclubs, and continental breakfast served on a balcony. There's a clothing-optional pool with a sundeck, plus a bar and a hot tub.

Equator Resort Key West is an all-male, clothing optional environment that prides itself in guest privacy and comfort. Tucked away in the heart of Old Town Key West in Fleming Street it's made up of several restored turn-of-the-century buildings just a 6-minute walk from the bars and restaurants on Duval Street. Casual rooms offer free Wi-Fi, minifridges, microwaves and flat-screen TVs. Some rooms have balconies or private patios, whirlpool tubs and/or wet bars. They have a continental breakfast and a nightly happy hour with cocktails. There's also an outdoor pool and a hot tub.


While you are in Key West you must visit The Hemingway Home and Museum where author Ernest Hemingway, famous for combining both genders, lived and wrote for more than ten years. Also worth a visit is the fascinating Mel Fisher Museum which hoards the recovery of $200 million-worth of gold and jewels from sunken Spanish ships and galleons.

New Orleans House on Duval Street in the center of Key West
Photo: RobertHoetink
If you enjoy travelling by boat you can try one of the LGBT clothing-optional Blu Q snorkelling or sunset sail excursions, complete with lunch and beer, oft served in the nude, on far-out waist-deep sandy bars – if you’re lucky, with the odd pod of stray gay-friendly dolphins thrown in! Check out the colourful and relaxing Butterfly & Nature Conservatory - do check out their facebook page. Enjoy a film at the Tropic Cinema, or a tour to American Civil War-era Fort Jefferson on the Dry Tortugas National Park Ferry and their Museum not far away in Margaret Street.


While in Key West you really have to try local island delicacies like succulent Key West pink shrimp or Key Lime Pie. Check out the magnifico Italiano food at classy Antonia's right in the centre on Duval Street, or the well-priced Harpoon Harry's on Caroline Street - they also make for a perfect breakfast option.


If you are in search of some cabaret, try the ever popular 801 on Duval Street or nearby La Te Da which is a stylish Piano Bar with some amazing vocal talent. If you'd rather dance then Bourbon Street also on Duval Street, is the place to head for and it includes a rear garden bar, pools and cruisy terraces.

Then there's Aqua just the down the road, with their famous Aquanettes, entertaining you with some drag. In complete contrast there's One Saloon, in Petronia St, behind 801 which historical gay watering hole with late hours, drink specials, live entertainment & an outdoor patio. The venue specialises in Leather 'n' Levis, with a regular Cock Shock at Midnight on Fridays, when you can leave your inhibitions behind!

Bobby's Monkey Bar is a super fun bar with nightly karaoke. You can see locals, gay and straight, all in one place. It's easy to be dragged in to getting up to sing a few songs. Sidebar Key West is more of a dance club with live DJ's nightly and theme party's weekly. It is open for a happy hour every day early in the evening and they have a free pool and lounge. There's an outdoor restaurant and what they say is KW's hottest late night dance floor.


Most national carriers fly in to Miami airport – American Airlines offering some of the best fares and the very best in-flight entertainment around. From Miami it's a Technicolor 150 mile road movie advernture (Greyhound Bus or Mini-Van Shuttle) down to Key West itself! Or jump a popular American Eagle (part of American Airlines), twin-prop from Miami to save on time.

Every Saturday morning at 11 the Gay Trolley Tour chronicles the history of gays and lesbians in Key West and the impact they had on the island. You'll see Tennessee Williams' house, Jerry Herman's restored twin houses and see why on the Island of Key West being gay is just a part of life.
Photo courtesy Key West Business Guild.


Gay Key West Florida
Florida Keys
Florida Keys - Key Voices


801 (801 Duval Street; T: +1 305 296 1992; Website)
Alexander's (1118 Fleming Street; T: +1 305 294 9919; Website)
Antonia's (615 Duval Street; T: +1 305 294 6565; Website);
Aqua (711 Duval Street; T: +1 305 294 0555; Website)
Blu Q (200 Margaret Street; T: +1 305 923 7245; Website)
Bobby's Monkey Bar (900 Simonton St; T: +1 305-294-2655)
Bone Island Bare It All (Website)
Bourbon Street (724 Duval Street; T: +1 305 293 9800; Website)
Butterfly & Nature Conservatory (1316 Duval St; T: +1 305 296 2988; Website)
Dry Tortugas National Park Ferry (300 Grinnell Street; T: +1 800 634 0939; Website)
Dry Tortugas National Park Museum (240 Margaret Street; T: +1 800 634 0939; Website)
Equator Resort Key West (822 Fleming St; T: +1 305-294-7775; Website)
Fantasy Fest (Website)
Harpoon Harry's (832 Caroline Street; T: +1 305 294-8744; Website)
Island House (1129 Fleming Street; T: +1 305 294 6284; Website)
Key West Bear Weekend (Website)
Key West Pride (Website)
La Te Da (1125 Duval Street; T: +1 305 296 6706; Website)
Mel Fisher Museum (200 Greene Street; T: +1 305 294 2633; Website)
New Orleans House (724 Duval St # 2; T: +1 305-293-9800; Website)
One Saloon (504 Petronia St; T: +1 305 294 4737; facebook)
Sidebar Key West (504 Angela St; T: +1 305-294-1522; Website)
The Hemingway Home and Museum (907 Whitehead Street; T: +1 305 294 2755; Website)
Tropic Cinema (416 Eaton Street; T: +1 877 761 3456; Website)

Revised June 2023.


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