Key West: Where the Wild and Weird Go Pro

Kevin Ruck/Shutterstock.com

The quirky queer utopia at the end of the road.

If your only image of Key West is a Jimmy Buffett-meets-Hunter S. Thompson fever dream filled with Hawaiian shirts, fancy umbrella drinks, and drunk spring breakers taking their clothes off in public, you’re due for an enlightening. Of course, tourist traps (crude $5 T-shirt, anyone?) and inebriated, half-naked tourists abound, but for the most part, life tends to lean to the endearingly quirky side down on the southernmost tip of the United States.

The island, which was originally called Cayo Hueso (literally “bone cay”) due to its use as a communal graveyard by prior native inhabitants, attempted a tongue-in-cheek secession from the U.S. in 1982, citing a U.S. Border Patrol blockade on U.S. 1 as cause for (non-violent) civil war. Its “war” with the U.S. may have only lasted moments, but its declaration of independence became an excuse for an annual island-wide party each April. And no disrespect to RuPaul, but it was during one of these so-called Conch Republic Day celebrations that the original “drag race” — that is, a bunch of men racing down the street and dodging obstacles in heels — was born.

Indeed, Key West knows how to party. Take Fantasy Fest, for example. Whereas everyone else in the U.S. celebrates Halloween for one night, Key West stretches out the festivities for ten costumed, body-painted, intoxicated days. You might see a lot of things you’d rather forget, but you’ll have a damn good time doing it.

The days seem to slow down here, and “island time” is alive and well. You won’t find anyone walking at a New Yorker’s pace on an afternoon bar crawl and you might catch a business or two hanging a siesta sign around lunchtime. Drinking is a natural part of the day and is hardly ever frowned upon “as long as you show up for work sober — okay, well, sober-ish,” according to one local.

But there’s so much more to Key West than Margaritaville and the other dens of drink on Duval Street. Walk through the quaint streets of Old Town Key West and you’ll find houses decorated as if it’s Halloween and Christmas year-round, with perfectly manicured lawns studded with flamingos, skeletons, and twinkle lights (and, more often than not, all three). Chickens and iguanas cause traffic jams while they soak up the sun. One local dive bar, Mary Ellen’s, even holds vibrator races (yep, exactly what it sounds like) every Thursday night. (Go for the vibrator races, stay for the grilled cheese and frozen Irish coffees — trust me.)

The official motto of the Florida Keys tourism board is “Close to perfect, far from normal,” and nothing could more succinctly sum up the idyllic-yet-offbeat vibe of this peculiar slice of paradise. To put it bluntly, Key West is weird. And to truly experience the magic of the island, you’ll want to embrace it.

801 Bourbon Bar / Photo courtesy of 801 Bourbon Bar

Cuban Coffee Queen / Photo by Mike Cherim/Shutterstock.com

First of all, ditch the car. Rent a bike and cruise around town like the locals do (I recommend Island Bicycles, Eaton Bikes, or We Cycle). Start your day off with a café con leche and a pan Cubano (always delicious) — Key West is only 90 miles away from Cuba, after all. Spend the day sunning your buns at Fort Zachary Taylor State Beach, learning about the history of the island (the Custom House Museum is as informative as it is interesting, and you can’t leave town without seeing Hemingway’s six-toed cats at the Hemingway House), or immersing yourself in beautiful flora and fauna (the Butterfly Conservatory isn’t the top-rated attraction for nothing).

And let’s not forget the real draw of Key West: It’s a queer heaven. A whopping 30% of the island’s 25,000 year-round residents identify as LGBTQ+. The island’s history as a gay destination dates back to the 1950s, when well-known LGBTQ+ celebrities like Truman Capote, Tennessee Williams, Gore Vidal, Leonard Bernstein, and Elizabeth Bishop made it their home. And in 1983, Key West became the first place in the U.S. to elect an openly gay mayor, Richard A. Heyman. Then, in 2000, the island adopted the official motto “One Human Family,” proclaiming itself welcoming to anyone and everyone.

There was not a street I walked down where same-sex couples weren’t holding hands. Drag queens hung out on Duval Street during the day, fully made up and fierce. Gay couples cuddled together under the warmth of the sun on boats and in bars.

Every watering hole I checked out was the perfect mixture of dive bar and gay club, where everyone is welcome to drink and dance regardless of their sex or orientation. Same-sex couples can feel comfortable expressing PDA — anything from hand-holding to full-on making out — anywhere they go without a second thought. This be-whoever-you-are ambiance is so ingrained in the island’s culture that the kids who grow up there “are all sexually fluid, because they’ve never been taught that there’s anything wrong with that,” one local told me over a slice of key lime pie at a neighborhood diner.

The community is open to embracing whoever is next to fall prey to the island’s allure, as so many have before — including Jimmy Buffett, Kenny Chesney, Shel Silverstein, and local bookstore owner and legendary coming-of-age novelist Judy Blume. Greg, a representative from the tourism board, kept telling me that many of Key West’s residents originally came to visit and never left, but I struggled to believe him until I headed to the island myself. Very quickly, I saw what Tennessee Williams and Ernest Hemingway had found so compelling decades before: a beautiful and lively locale. Nowadays, Key West is overflowing with activities like sunset cruises, jet ski tours, snorkel trips, and floating bars. Everywhere you look, you’ll find breathtaking views and exotic wildlife (and also a lot of roosters and iguanas). And the centerpiece of it all is the dynamic and queer-friendly main strip, Duval Street, which is home to many of the island’s most popular restaurants, nightlife, and shops.

Duval Street is also where you’ll find the Key West Business Guild, the nation’s first LGTBQ+ destination marketing organization, whose mission since 1978 is to promote Key West to LGBTQ+ travelers (so you can thank them for making Key West the gay spot it is). Back when the LGBTQ+ community was forced to exist on the fringe, Key West was one of the few accepting, come-as-you-are travel destinations where LGBTQ+ visitors were free to express themselves in all their queer glory. That mentality has only expanded, thanks to the Key West Business Guild. In fact, the nonprofit organization’s marketing campaigns help attract about 250,000 LGBTQ+ travelers to Key West each year, cementing the island’s reputation as one of the most gay-friendly destinations in the world.

Key West is an alternate utopian world where everyone can live how they want, love who they want, and just try to enjoy it all while they’re here. It’s a place that embraces and celebrates diversity. It’s a lofty goal for one tiny little island, to be sure, and yet, if there was ever a community capable of doing so, there’s no doubt that an island whose official motto is “One Human Family” is ready to take on the challenge.

If you’re hoping to dive into tropical queer bliss for your next vacation and you want our personally vetted recommendations, we’ve got you covered with the best (and gayest!) in where to stay, where to eat, and what to do.

Key West locals at Pride / Photo courtesy of Key West Business Guild

Bad Boy Burrito fish tacos / Photo by Isabelle Lichtenstein

Where to Stay

If you’re looking to feel like a local during your stay, skip the Hyatt or the Casa Marina and stay at a local guesthouse instead. Key West has a number of guesthouses spread across the island, either amid the action of Duval Street or tucked away in quieter and more residential neighborhoods. Full disclosure: A handful of the smaller guesthouses cater exclusively to gay men, but there are still more than enough off-the-beaten-path options for the dames. Unfortunately, the only lesbian-focused guesthouse, Pearl’s Rainbow, relaunched as an open-to-all business instead, but there are still many LGBTQ+-friendly guesthouses where queer women will feel comfortable.

My personal recommendation is Alexander’s Guesthouse (alexanderskeywest.com). While the guesthouse is open to all visitors, Alexander’s largely draws queer travelers. There are rainbows everywhere — on the back of staff shirts, on the entrance sign, by the pool — that remind you constantly that you’re in a gay-friendly space. Boasting a 24-hour pool and jacuzzi, this is the kind of place you look forward to coming home to after a fun day out. Alexander’s Guesthouse is also frequently the headquarters for Key West Womenfest (more on that later), which gives them added lesbian street cred. Make sure you hit happy hour at their onsite bar, the Pink Monkey Bar. Pro tip: Try to book room 14 — it has a Jacuzzi right outside.

If you want to be right in the heart of the action, LaTeDa (lateda.com) is smack in the middle of Duval Street. The 15-room hotel is adults-only and houses a restaurant and two separate cabaret venues, where drag queens Randy Roberts and Christopher Peterson perform just about every night. Every Sunday afternoon, LaTeDa hosts Tea Dance, a fun, inclusive event for locals and visitors that takes place outside by the pool and features great dance music played by local (and lesbian) DJs Rude Girl and Molly Blue.

If you would prefer the feel of a traditional hotel, check into the über luxurious boutique Marquesa Hotel (marquesa.com). Set in the center of the historic district, the Marquesa is located within walking distance of Duval Street, as well as a number of other island sights. The hotel, a beautifully renovated 19th century Conch cottage (that’s Key West speak for an old island house), is split into two separate yet adjacent properties, and both are set around an interior garden and outdoor pool. It’s a bit fancier than your average guesthouse and perfect for doing Key West in upscale style.

And if you’re on a budget, look into the hostel-like NYAH (Not Your Average Hotel) (nyahotels.com). NYAH has 36 rooms, each of which sleeps up to six people. Their BYOR (Build Your Own Room) concept allows you to stay solo or with a group of gals at the same price, so you can travel in a pack and then spend your hard-earned dollars eating, drinking, and playing your way around town.

A cat at the Hemingway House / Rob O’Neal

Bikes on break / Photo by brians101/iStock.com

Where to Eat

After getting settled, finding great food should be next on your list (it was on mine, at least!). Key West is home to too many delicious restaurants to count, and many take inspiration from the abundance of fresh seafood and the island’s historic influx of Cuban and Caribbean residents.

If you want someone else to do all the menu planning while you just tag along for the ride, let Key West Food Tours be your guide (keywestfoodtours.com). Their original tour, the Southernmost Food Tasting & Cultural Walking Tour, allows you to indulge in must-try, iconic Key West dishes — deliciously deep fried conch fritters, fresh fish tacos, the famous key lime pie, and more. The Seafood Lover’s tour lets you sample six local seafood specialties, ideal for those who are more inclined towards fresh catch and crustaceans. And lastly, the Key West Bar Crawl is a sip and stroll tour of Key West’s craftiest bars and hidden local gems. In addition to the food and drink, you’ll get loads of fun facts and historical tidbits.

One of my favorite stops was Bad Boy Burrito, which operates out of a small walk-up window attached to the BottleCap Lounge on Simonton Street (badboyburritokeywest.com). Don’t let the size deter you from trying this local favorite that features fresh, local fish in its addictive tacos and burritos. While you can find classics like mahi mahi and lobster on the menu, the restaurant is committed to using lesser-known fish (golden tilefish, anyone?) and celebrating Key West-specific catches. You never know what the fish of the day will be, but it’s certain to be delicious. Plus, the BottleCap hosts hilarious comedy shows on Thursday and Friday nights, so you can have your burrito with a side of stand-up.

A cyclist rides by blue heaven, a restaurant favored by locals and visitors alike / Photo by Andy Newman

An aerial view of Fort Zachary Taylor Beach / Photo by Rob O’Neal

Of course, you can’t go to Key West without trying the famous key lime pie. While seemingly every business offers a slice, some are better than others. I lucked out trying the personal size pie at Blue Heaven (blueheavenkw.com). Tart, creamy and topped high with toasted meringue, this treat was unforgettable. Plus the all-day live music put me right in an island state of mind.

For brunch any day of the week, head to Moondog Café & Bakery (moondogcafe.com) on Whitehead Street, right across the street from the Hemingway House. Not only does the kitchen whip up eggs benedict five ways and a shakshuka that could make you cry spicy Mediterranean tears, but it also serves a delicious lunch and dinner menu. The Frenchman burger, with crispy onions, brie, roasted honey-garlic jam, and arugula, is the definition of decadence, while the roasted mushroom, truffle, and fontina pizza will make you feel like you’re in a piazza in Italy. Who says you can’t eat there twice in one day? Plus, the onsite bakery is constantly churning out tasty treats, many of which are gluten free and vegan, in case you need to feel a little virtuous while you’re polishing off that third mimosa.

Azur (azurkeywest.com) is a partially gay-owned upscale Mediterranean-inspired restaurant. Go gung-ho on seafood here, as fish are the crown jewels of the menu. Azur also has some delicious meat and vegetable options, but my favorite is their selection of soft, pillowy gnocchi — I have been dreaming of the toasted gnocchi with pine nuts, truffle, and arugula since I left town.

Little Pearl (littlepearlkeywest.com) is hands down one of the most creative restaurants in Key West. The space is cozy and intimate — perfect for a romantic dinner a deux — and the menu highlights local seafood using unconventional techniques (sorry, but you won’t find fish tacos here). Start with the Bangkok octopus, indulge in the Little Pearl lobster, shrimp, and crab pot pie, and wrap it all up with the Moscato and ginger poached pear with vanilla ice cream.

Key Lime Pie from Blue Heaven / Photo by Isabelle Lichtenstein

Gay Pride catamaran cruise / Photo by Larry Blackburn

What to Do

You can’t come to an island without expecting some beach time. For that, head to Fort Zachary Taylor State Park (fortzacharytaylor.com). It’s the cleanest and least crowded beach, and the locals flock there when they want to catch rays in peace. Some residents lovingly refer to it as Elizabeth Taylor State Park, “just to make it gay,” as one person told me.

Try not to spend your whole vacation lounging on the beach when there are so many other water adventures to be had. Head to the lesbian-owned Lazy Dog Adventures (lazydog.com) for kayaking, paddleboarding, and boat-based eco-trips. Lazy Dog offers paddle yoga classes, day-long workshops, and eco-tours of the island via the water — expect to see rays, starfish and all manner of aquatic fauna. Or rent your own floating tiki bar from Cruisin’ Tikis Key West (cruisintikiskeywest.com) for a sand-bar-hopping or slow-moving sunset cruise. Your own personal tiki hut seats up to six people for a buoyant, guided island tour with BYOB food and cocktails.

Stormy days are perfect for exploring the Key West Butterfly & Nature Conservatory (keywestbutterfly.com). Full of beautiful exotic birds (including Rhett and Scarlett, the resident flamingoes) and, of course, butterflies, it’s a beautiful indoor spot to get lost in.

You can also spend the day learning about one of the island’s most famous residents: Ernest Hemingway. Take a tour of the Hemingway House (hemingwayhome.com) and witness the beauty that inspired one of the world’s most well-known wordsmiths. Check out Hemingway’s lasting impact on the island, from the works that he created while living there to his affinity for breeding six-toed cats — dozens of which still adorably roam the property.

Your trip to Key West is only as gay as you make it. To get your queer-oriented bearings, stop into the Key West Business Guild (gaykeywestfl.com) on Duval Street and find out about all the awesome LGBTQ+ events and businesses in the city. Right around the corner is a gem: the Tennessee Williams Museum (kwahs.org/museums/tennessee-williams). One of America’s foremost playwrights, Williams (who was gay) lived in Key West for many years. Stroll through this small-but-mighty museum and browse his books, photographs, paintings, and even one of his typewriters.

A close-up of a butterfly at the Key West Butterfly & Nature Conservatory / Photo by Isabelle Lichtenstein

Key West Womenfest attendees poolside / Photo courtesy of Key West Business Guild

Where to Party

When it comes to all things woman, Womenfest (gaykeywestfl.com/womenfest) is the lesbian event that rocks the island every year. For decades, Key West’s Womenfest weekend has drawn thousands of lesbians and their friends to the city over Labor Day weekend with a simple goal: to serve as a gathering for women who want to mix, mingle, feel comfortable being themselves, soak up some rays, and then party their faces off. The typical schedule of events ranges from raucous pool parties to intimate art openings, but much of the draw of Womenfest is the simple promise of lazy days spent poolside or strolling through the sun-dappled historic neighborhoods of Key West with the comfort of knowing you can hold your girlfriend’s hand without some psychopath yelling hateful slurs from across the street.

For a more inclusive LGBTQ+ experience, you can’t miss Key West Pride Week in June, when the island reaches peak rainbow peacock status. From fetish parties to universally inclusive church services, Key West Pride is always decadent and iconic. And in the charged and ever-changing political climate of America’s LGBTQ+-rights movement, celebrating Pride Week in the city that helped define gay pride serves as a reminder of just how important it is to celebrate such things, lest we forget how hard they were fought for, and how vital it is we continue to fight to ensure their future survival.

While Key West Pride is certainly not the largest festival of its kind, it carries with it the momentous importance of celebrating the island’s gay ancestry and does so with the kind of gaudy antics that Key West is famous for. Classic events such as clothing-optional gay sailing and snorkeling tours, cocktail competitions, drag shows, and all manner of themed parties are held across five revelry-packed days. And while many of the events scheduled for Pride Week are undoubtedly adults-only, Key West Pride also includes many kid-friendly events for gay families traveling with children who wish to celebrate Pride in a more PG-setting, including a variety show, multiple church services, and the annual Duval Street Fair.

The outside of the Speakeasy Inn and Rum Bar / Photo courtesy of Speakeasy Inn and Rum Bar

The owner of Lazy Dog Key West with her pup / Photo courtesy of Lazy Dog Key West

But if you can’t make it down for Womenfest or Pride Week, there’s plenty more social lesbian fun here all year long. If you’re looking to hit the LGBTQ+-focused bars, it’s best to head to what locals call the “Pink Triangle,” aka the 700-block of Duval Street. It’s home to dance clubs, low-key bars. and whatever flavor of nightlife you crave.

For dancing, head to Aqua Bar and Night Club (aquakeywest.com). It’s a mixed LGBTQ+ crowd, so you’ll be able to bring your gay guy pals and each find a hottie to go home with. Aqua hosts acclaimed nightly drag shows and the gorgeous queens are constantly roaming around this hotspot, so be sure to bring your dollar bills if you stop by. Make sure to check out Hot Dog Church with badass (and immensely charming) lesbian bartender Laurie Thibeau on Sundays. Lesbian ladies gather at Aqua’s Back Bar every Sunday at 3:30 p.m. — sometimes hot dogs are grilled (hence the name), but more often than not it’s a potluck-style, estrogen-filled kibbitz. Aqua also plays host to several events for Womenfest and during Pride Week, making the Aqua Nightclub complex a safe and welcoming space for us ladies year-round.

801 Bourbon Bar (801.bar) is right down the block from Aqua. This spot hosts nightly drag shows upstairs, while downstairs is the place to have a good drink, an interesting conversation, and a little dance break to a top 40 hit. Straight tourists find their way here to watch the infamous drag shows, but it’s still a favorite for queer locals.

For divey karaoke fun, try the beloved and highly under-the-radar Bobby’s Monkey Bar (bobby-s-monkey-bar.hub.biz). It’s nothing fancy, but it’s an unabashedly good time filled with chain-smoking, country music-singing locals. Order a (very strong) drink, sing whatever song is in your heart, and prove to the regulars you can be just as rowdy as they are.

On the opposite side of the spectrum is the Rum Bar (speakeasyinn.com/rum-bar/). The sophisticated, speakeasy-style watering hole sets itself apart by fully committing to its titular liquor. It is home to over 350 rums from all over the world, and the bartenders are essentially rum sommeliers — ask them anything about the spirit. Then enjoy a phenomenal Rum Runner, the unofficial drink of the Florida Keys.

Finally, if you happen to be on the island on a Sunday, finish off your very gay day with Not Your Momma’s Bingo with the fabulous drag queen QMitch at the 801 Bourbon Bar Cabaret. Or head to LaTeDa for its beloved Key West Tea Dance (lateda.com/tea-dance). Shake your tail-feathers to some bumping music, enjoy the queer company for high tea, and soak up your surroundings on this one-of-a-kind island. You’re in paradise, after all.

The “Sea to Sea” rainbow flag at Key West Pride / Photo by Andy Newman

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