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Key West: Fantasy Now, Always

Travel Tips | Jim Werner | October 5, 2023

Ernest Hemingway wrote, “Everyone behaves badly — given the chance.” Yes, old Ernie must have been talking about Fantasy Fest in Key West.

The southernmost island of everyone’s favorite archipelago lures travelers year-round. A come-as-you-are spirit, tropical atmosphere, beautiful landscaping, crystal water and clothing-optional attitude — what’s not to love? Key West means happiness.

Always ready for a party, Cuba’s tiny neighbor amps it up during Fantasy Fest, a 10-day, no-holds-barred fête filled with costumes, body paint, drinking, dancing, life loving and skin aplenty. I consider it a high holy day (lowercase; no offense here!) and fly south for it every year, meticulously planned outfits in tow. The celebration — themed “Uniforms and Unicorns” for 2023 — is going down later this month from October 2029, 2023.

Headed to the bash? Still thinking about going to the party? Here are the highlights. Can’t make it? Keep scrolling down to the anytime suggestions for your off-Fest Key West getaway.

Fantasy Fest Highlights for Gay Men

Two men wearing identical bloody shirts and shorts for Fantasy Fest's Zombie Bike Ride.

Zombie Bike Ride

The Sunday zombie bike ride kicks off the festivities with thousands of undead cyclists taking to the streets in their gory best. It doesn’t matter if you’re a seasoned rider or just looking for some spooky fun, this event is not to be missed. Head to Bourbon Street Bar for the afterparty.

Four individuals wearing leather attire and masks socialize at a bar.

Tops or Bottoms Underwear Party

Let it all hang out (or keep it covered, your choice) at this iconic Monday night party. Held at the Bourbon Street Pub, this is a night of uninhibited fun. You’ll have a blast no matter how much or little clothing you decide to wear. This one is for men only.

Two men and one women wearing witch costumes, complete with pointed hats and tutu's pose for a Halloween-themed photograph at Fantasy Fest.

Tutu Tuesday

Get creative with your tutu — you know you have one — for this crazy-fun party. It starts off with a short march around the island stopping at some popular spots and ends at 22&Co for the official event. Note: You must be wearing a tutu for entry. And why not, right?

Desire Male Fetish Party

Likely named by a straight-shooter kind of guy, this Wednesday night event at New Orleans House Garden & Pool Bar shouldn’t require much explanation. You can watch the action from the sidelines or get hands-on to explore your inner desires. Saucy.

Several men, clad in underwear, getting ready for exposed party at Fantasy Fest.

Exposed at the Bourbon Street Pub

Pool, hot tub, foam — and that’s just outside. Indoors at Bourbon Street Pub, DJs, exotic dancers, glow sticks and big screens broadcasting fantasy scenes set the mood for Thursday’s all-nighter. Don’t know what to wear? Let’s just say that you need not worry about that here.

A group of guys dressed as aliens in the colors of the Pride rainbow flag at Fantasy Fest in Key West for a top LGBTQ+ Halloween event

Captain Morgan’s Masquerade March

Crowds make their way through Old Town to the tune of music and noisemakers during the Masquerade March, also known as the People’s Parade, on Friday. Join at any point along the route (step-off is at the Key West Cemetery) and take drink breaks at participating guesthouses along the way, including the all-male clothing optional Equator Resort.

Bud Light Fantasy Fest Parade

Happening on Saturday evening, this is the main event, so try to save some energy for it. Pimped-out floats, extravagant costumes and fabulous performances take over Duval Street. It’s like a Super Bowl parade. And everybody wins at Fantasy Fest.

Two guys dressed as Waldo for Fantasy Fest

Tea Dance

As Fantasy Fest whirlwind begins to settle, the Sunday Tea Dance at La Te Da is your cool-down party. This is your chance to show off your creative side, whether that’s tropical chic, outlandish glam or one final costume. And hey, it’s a tea dance, but sunscreen is the real ‘tea.’ Wear it generously unless you fancy a facial tan line as a souvenir of this wild week!

Survival tip: You’ll wear costumes every day, and people take them very, very, very seriously. Do not slack off. (Secondary tip: There’s no such thing as “too risqué.” Be sure to grab something from the fetish collection of the gay-owned menswear designer, Addicted USA, and you’ll be good to go.)

Key West (All the Time)

Rainbow Crosswalks: Spanning all four corners at the intersection of Duval and Petronia streets in the heart of the LGBTQ entertainment district are long bands of the six colors of the rainbow flag for the perfect instagram-worthy pic.

Harpoon Harry’s: Start the day off right with a hearty breakfast. You’ll probably need to soak up the residual beverages floating around in your system from the previous night. The food is basic yet delicious. Think alfresco greasy spoon. You’ll be back for more before the end of your stay.

Graffitti Menswear: Between swimming, relaxing, sunning, drinking and dancing, you may find spare time to hit the town’s stores. Put Graffiti Menswear on the top of that list for modern and hip (does saying “hip” make me unhip?) clothes. The house music may inspire you to venture into edgier territory.

Lola’s Bistro: This intimate BYOB substitutes an elegant dining experience for the kitsch common in many Key West restaurants. The rotating menu is unreal, and the portions will actually fill you. Leave room for the carrot cake – a nice departure from the islands famous Key lime pie.

801 Girls Cabaret: I cannot emphasize this enough: 801 Girls is an absolute must-do in Key West. The twice-nightly shows end up being different every time the ladies take the stage. So, it’s worth hitting up the 801 Bourbon Bar event a few times while you’re on the island.

Fury Water Adventures: Get out on the water with some high-adrenaline activities and sports – and no, we’re not about that kind of water sports. Some of their more popular options include full-day excursions for parasailing, jet skiing, kayaking, and snorkeling.

Ghosts & Gravestones of Key West: Perhaps one of the most haunted cities in America, Key West has no shortage of ghost stories and spooky haunts. Experience the undead or learn about it from the safety of a trolley.

Bourbon St Pub by flickr user jbetac

Wrapping Up Your Key West Adventure

So there you have it, folks! A little slice of paradise, a sprinkling of Hemingway, and a dash of non-stop partying, Key West has it all. Even if you can’t make it for the high-energy Fantasy Fest, don’t worry — Key West’s spirit of fun and freedom is a year-round affair. So, go ahead, pack those flip-flops, let your hair down, and get ready for an unforgettable adventure. Because in Key West, it’s always time for a great time. See you there, maybe?


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Photos by Flickr users JBetac used under the Creative Commons Attribution license and courtesy of Larry Blackburn

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And let’s be honest, that’s pretty darn gay.

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