Key West

© Dirk Baumgartl


Classic, comfortable and gay. The Island House (1129 Fleming St) is the perfect place to stay. The in-house fitness studio is also accessible to locals, the menu in the pool restaurant is good and varied, every evening there’s a happy hour with free drinks. The guests arrange everything else among themselves. Some rooms have shared bathrooms –  for the extra sociable -, and if you need to do a bit of work during your holiday there a suites available that have their own office.

© Island House Key West

New Orleans House on Duval Street (724 Duval St), the only guest house hosting gay men only, places fun on your holidays before everything else. There are few dress codes and the pool is a great place to relax even after a few drinks. Particularly popular are the shows during events such as the Fantasy Fest, the Pride or the famous Great Conch Republic Drag Race.

© New Orleans House / Bourbon Street Pub

The Equator Resort (822 Fleming St) has a Mediterranean ambience. As in other gay resorts, you can splash naked in the pool or lie on the whirlpool terrace and have free drinks at happy hour. The atmosphere is calmer and the guests are a little less focused on party.

As Gay & Lesbian Guest House Alexander’s Guest House (1118 Fleming St) is also aimed exclusively at adults. In this way, the operators guarantee their guests the peace and quiet that defines the luxurious overall atmosphere.


The Bagatelle (115 Duval St) has rightly received several awards for its excellent cuisine and is famous for its award-winning wine selection. The menu includes steaks as well as fish and lobster specialities. The restaurant is located in a renovated house from the 19th century and exudes a cosy atmosphere despite its exclusivity.

An excursion to the Waterfront Brewery (201 William St), opened in 2015, is already worth the effort because of the pretty pier labyrinth at the harbour. Here you can enjoy a hearty American meal with a view of the water and try different beers from the in-house brewery. Guided tours are also available.

The Sloppy Joe’s (201 Duval St), once the regular bar of drinking specialist Ernest Hemingway, is a tourist magnet. The spacious Southern ambience is totally non-gay, but scores with live music every evening and the proximity to Mallory Square.

© Rob O’Neal


Key West’s lifeline is Duval Street. Here, where one bar is adjacent to another and one restaurant to another, there is something for every taste and budget, from a fast-food shed to an upmarket restaurant. It’s best to just to go with the flow without a specific aim in mind.

A must for gay night owls: the prestigious façade of Bourbon Street Pub (724 Duval St) hides a courtyard featuring a pool framed by various bars and terraces. You can drift from one level to the next and flirt with the joyous guests.

Opposite the Bourbon Street Pub is the 801 Bourbon (801 Duval St). After more than three decades of existence, the shop is its own legend. Its nostalgic charm is mainly due to the drag queens that perform here every evening.

For those who prefer it down-to-earth, Bobby’s Monkey Bar (900 Simonton St) is the place to be. In “Key West’s Favourite Local Bar” you meet many local regulars who don’t show up in the tourist bustle on Duval Street. The playlist is determined by an impressive karaoke catalogue, which is eagerly sung at sight by queer boys to grandmas with zimmer frames.


Ernest Hemingway lived in Key West from 1931 to 1940. Besides original furniture, most of which Hemingway and his second wife Pauline imported from Paris you can discover eccentricities in the Ernest Hemingway Home and Museum (907 Whitehead St), such as a fountain in a disused urinal from Hemingway’s local pub Sloppy Joe’s (see above). The house also is home to several dozens of cats all of whom are said to be descendants of Hemingway’s favourite pet, Snow White. Admission: 14$ including a guided tour.

© The Hemingway House and Museum

The free Tennessee Williams Key West Exhibit about the gay playwright Tennessee Williams is located in the same building as the Pride Club (513 Truman Ave, see below). Willams, who lived in Key West from 1948 until his death in 1983, did not live in this house, though. The collection of photographs, posters and manuscripts do hot have the sane authentic flair as Ernest Hemingway Home, but aficionados get an impression of the time Williams spent in Key West.

© Laurence Norah Florida Keys News Bureau


At the entrance to Key West, the Ibis Bay Resort (3101 N Roosevelt Blvd) not only houses the fantastic seafood restaurant “The Stoned Crab”, but is also the starting point for Ibis Bay Paddle Sports, guided stand-up paddle and kayak tours. A highlight are the nocturnal trips with illuminated glass-bottom kayaks, during which you first search the shallow seabed for fish, crabs and sponges. You finally glide over the sheer of a large reef while thick lobsters are hiding in the sea grass.

The Key West Lime Bike Tours are called such, because every ride ends with a Key-Lime-Pie dinner. The lime cake with the meringue hood is a local speciality that is offered in various fashions all over the Keys. The dessert is particularly palatable at the end of a guided bike tour. You can explore the sights on bright green bikes while friendly guides offer you profound commentary.

© KeyLimeBike

Every evening at sunset, Mallory Square at the end of Duval Street is filled with jugglers, musicians and onlookers celebrating the dawn of the night with the Sunset Celebration. While cruise ships anchor on one side and the silhouette of the uninhabited island Wisteria is disappearing in the sunset on the other, everone gets into party mood.


© Dirk Baumgartl

Another nice way to enjoy the sunset is a Sunset Catamaran Tour with Sebago (205 Elizabeth Street, Unit I). While you rush out to sea with fluttering sails, there are snacks, beer and margaritas available until you can no longer tell the rocking of the waves from the swaying fom being tipsy. Cost: about 40 dollars per person.


The Conch Republic Independence Celebration is a fun ten-day event (20 to 29 April 2018) whose highlights include the legendary drag race, the coronation of the “royal family” and a parade.

© New Orleans House

Formerly called Gay Pride, now Key West Pride, the action has remained the same: Five days of non-stop party (June 6-10, 2018) and a parade that makes Duval Street look like the gayest street in the world.

© promo

The Tropical Heat is a gay festival that does justice twofold: to the heated programme of its name and taking place in the hottest month (15 to 19 August 2018), offering lots of cruising parties.


In his volume of essays Where I Live, Tennessee Williams has also included a text about “his” Key West. Tennessee Williams: Where I Live. New Directions Paperbook, 313 pages, approx. 17 Euros, in English.

To have and not to have is one of Ernest Hemingways’ rather unknown novels. The author wrote most of it in Key West, several stories are also set here. Ernest Hemingway: To have and not to have. Rororo, 160 pages, 9 Euros.

The bittersweet novel The Shining Memory of Michael Zadoorian has just been turned into a movie starring Helen Mirren and Donald Sutherland and is about a couple that make a road trip to Ernest Hemingway Home as the man’s Alzheimer’s disease gradually progresses. Michael Zadoorian: The glow of memory. HarperCollins, 304 pages, 13 Euros.

Even the trailer for the Netflix series Bloodline is like a promotional film for the Keys. Perfect to get into a tropical mood, even if the family drama that is told is rather gloomy.


There is a shuttle bus from Miami airport to the Keys, which must be booked 48 hours in advance via their website. The standard one-way ticket costs 90$, advanced saver fares are available., 


The Pride Club has its office at 513 Truman Avenue. If you want to get a first overview of the gay Key West, this is should be your first call. Apart from insider knowledge the boys at the reception also offer brochures and help with personal holiday planning.

The website of The Florida Keys & Key West offers a lot more information about Key West and the other islands (worth a visit) of the archipelago . The portal also gives an overview of the local LGBT community.

Share this article with your friends:

top hotels

Salvador - Bahia

Casa do Amarelindo

Charmantes 4-Sterne-Hotel, in einem restaurierten Gebäude aus dem 19. Jahrhundert untergebracht, im historischem Stadtt... more

Puerto Vallarta - Jalisco

Mercurio Hotel

Das Mercurio ist eine sehr gute Wahl. Es liegt in der Nähe des Strandes und der Szene und bietet einen schönen Pool. E... more



Das Amsterdamer Anco Hotel und seine Bar befinden sich in einem Haus von 1640 und heißen seit über 40 Jahren Ledermän... more