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Key West: Fantasy Now, Always

Travel Tips | Jim Werner | October 7, 2022

Ernest Hemingway wrote, “Everyone behaves badly — given the chance.” Yes, old Ernie knew 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 “Cult Classics & Cartoon Chaos” for 2022 — is going down later this month.

Headed to the bash? Still want to go to the party? Here are the highlights. Can’t make it? Keep scrolling down to the anytime suggestions for your off-Fest getaway.

Fantasy Fest (October 21 – 30)

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.

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.

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.

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 consider 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.

Note: During a previous stay in Key West some activities and meals were partially covered by the Monroe County Tourist Development Council. Rest assured the views and opinions expressed in this post are 100% our own and we would never sacrifice our integrity for a sponsorship.

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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