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Key West: Fantasy Now, Always

Travel Tips | Jim Werner | October 5, 2025

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

This southernmost island consistently lures travelers with its come-as-you-are spirit, tropical vibes, and clothing-optional attitude. What’s not to love? Key West is pure happiness. Always ready for a party, Cuba’s tiny neighbor dials it up during Fantasy Fest, a 10-day, no-holds-barred blowout of costumes, body paint, and unapologetic fun. I consider it a high holy day (lowercase, no offense!) and fly south annually with meticulously planned outfits in tow.

©JoeSwickFoto-2-XL_opt

What Is Fantasy Fest?

With a diverse lineup that includes both family-friendly and adult-only events, Fantasy Fest is a must-attend spectacle in Key West. Whether you’re a seasoned party pro or still on the fence about joining the revelry, there’s truly something for everyone: over-the-top parades, risqué soirées, wild bike rides, and even moments of pure Key West quirk.

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

Fantasy Fest 2025 Theme & Dates

If you’re already pondering your next outrageous costume, Fantasy Fest 2025 has unveiled its big theme: “Bedtime Stories & Magical Monsters.” Expect the Conch Republic to be overrun with fairy-tale heroes, creatures from the closet, and imaginative spins on your favorite childhood legends.

Mark your calendar: the island will be bursting with color and mischief from October 17 through October 26, 2025, along the spirited stretch of Duval Street.

Wondering just how many revelers pack the parade route? The Saturday night spectacle draws crowds of more than 70,000 eager partiers. It’s shoulder-to-shoulder along Duval Street as fans, friends, and every flavor of fabulous gather to watch.

What’s on tap for the theme week? Here’s a sneak peek of the can’t-miss action:

  • Goombay Festival: Bahama Village launches the party with Caribbean food and beats.

  • Royal Coronation & Headdress Ball: Drag royalty and extravagant headgear take over the Coffee Butler Amphitheater.

  • Key West Pet Masquerade: Pets in full fantasy drag — and yes, it’s exactly as amazing as it sounds.

  • Masquerade March: By Friday, costumed (and barely costumed) crowds snake through the streets.

  • The Big Parade: Saturday night, Duval fills with floats, dancers, glitter, and glorious mayhem.

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 as thousands of undead cyclists take to the streets in their goriest best. Whether you’re a seasoned rider or just seeking spooky fun, don’t miss this event. The afterparty is at Bourbon Street Bar.

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

Tops or Bottoms Underwear Party

Let it all hang out (or don’t, your choice) at this iconic Monday night party at the Bourbon Street Pub. This men-only night of uninhibited fun is a blast no matter how much—or little—you wear.

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 wild party. A short march around the island stops at popular spots before ending at 22&Co for the main event. Note: You must wear a tutu to enter. And why not?

Desire Male Fetish Party

Held Wednesday night at New Orleans House Garden & Pool Bar, this event doesn’t require much explanation. Watch from the sidelines or get hands-on and 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, and glow sticks set the mood for Thursday’s all-nighter. Worried about what to wear? Let’s just say you don’t need to be.

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 parade through Old Town on Friday to music and noisemakers during the Masquerade March, also known as the People’s Parade. Join anywhere along the route, which kicks off on Fleming between the Island House (named the best gay resort in the world) and the queer-friendly Alexander’s Guesthouse.

Deep Eddy Vodka Fantasy Fest Parade

Happening on Saturday evening, this is the main event, so try to save some energy. Extravagant floats, wild costumes, and fabulous performances take over Duval Street. Central to the festivities is the Key West Fantasy Fest Parade, rolling out on October 25 at 7 PM, where over 70,000 partygoers pack Duval Street to cheer on the show. The energy is electric, and the creativity knows no bounds. It’s like a Super Bowl parade. And everybody wins at Fantasy Fest.

Two guys dressed as Waldo for Fantasy Fest

Tea Dance

As the Fantasy Fest whirlwind settles, the Sunday Tea Dance at La Te Da is your cool-down party. It’s your final chance to show off your creative side, whether that’s tropical chic or outlandish glam. And hey, while it’s a tea dance, sunscreen is the real ‘tea.’ Wear it generously.

Extra Mayhem & Nightlife

For night owls and adventure-seekers, the island offers a host of bonus escapades — including late-night karaoke at gay-friendly Bobby’s Monkey Bar.

Ghost tours wind down narrow lanes past historic haunts if you want to get your spooky on (pro tip: costumes amplify the scares). Over at Sunset Pier and Duval’s open-air bars, live bands get everyone grooving as the sky turns magenta.

Love a splashy scene? Themed pool parties pop up daily, often at men’s resorts, promising cocktails, floating unicorns, and more bronzed skin than seems fair.

Survival tip: You’ll wear costumes daily, and people take them very, very seriously. Do not slack off. (Secondary tip: There’s no such thing as “too risqué.”)

Key West Beyond Fantasy Fest

Daytime Adventures: Breakfast, Beaches, and Bold Experiences

Harpoon Harry’s: Start your day with a hearty breakfast. You’ll probably need it to soak up last night’s beverages. The food is basic but delicious—think alfresco greasy spoon.

Rainbow Crosswalks (Well… Sort Of): Spanning all four corners at Duval and Petronia streets, the original rainbow crosswalks were recently painted over by the state of Florida in a classic DeSantis-era crackdown. But Key West doesn’t do erasure — the city responded by installing rainbow-colored bike racks in the same spot, keeping the spirit (and the photo op) alive in the heart of the LGBTQ entertainment district.

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.

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.

Nighttime Escapes: Fine Dining, Frights, and Fabulous Shows

Lola’s Bistro: This intimate BYOB offers an elegant dining experience. The rotating menu is unreal, and the portions will actually fill you. Save room for the carrot cake.

Red Shoe Bistro: Gay-owned and operated, Red Shoe Bistro has become one of Key West’s standout dinner spots — and TripAdvisor just named it the number one date-night restaurant in the U.S. The vibe is intimate, the service is personal, and the food is the kind you remember long after you’ve left the island.

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.

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.

Bourbon St Pub by flickr user jbetac

Wrapping Up Your Key West Adventure

So there you have it! A slice of paradise, a dash of Hemingway, and a non-stop party. Even if you miss 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. 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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