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Fantasy Fest 2022!

10/21/2022 - 12:00am to 10/30/2022 - 12:00am

2022 THEME: Cult Classics & Cartoon Chaos

Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement!

Schedule of EVENTS (subject to change) courtesy of FantasyFest.com. Visit their site for details and last minute changes!

SUNDAY, OCTOBER 16, 2022

LA TRATTORIA OCEANSIDE PRESENTS ZOMBIE BRUNCH

Zombie Brunch is just 2 short Blocks away from the East Martello where it all begins. All you can eat ! Full Bar! Grab a great brunch before you ride upon the hallowed grounds of Key West.

WEDNESDAY, OCTOBER 19, 2022

2nd ANNUAL FANTASY FEST AIR SEX CHAMPIONSHIPS

As seen on HBO, MTV, Bad Girls Club, America's Got Talent, GQ Magazine It’s a magical blend of coordination, showmanship, humor, and interactive storytelling. It’s a comedy show that brings people together in a respectfully dirty, unpredictably ridiculous, and oddly touching celebration of sexual freedom and expression. It’s neon-lit gyrating silhouettes. It’s organized confusion. It’s voyeurism 2.0.

SEXY BULL RIDING CONTEST

Cowboy Bill’s incredible Fantasy Fest Ladies Nite Party on Wednesday October 21. From 9PM – 11PM ladies drink free well drinks and draft beer. Then at Midnite, turn up the heat with one of the wildest events of Fantasy Fest, Cowboy Bill’s Infamous Sexy Bull Riding Contest.

THURSDAY, OCTOBER 20, 2022

COWBOY BILL'S 13th ANNUAL GIT-R-WET T-SHIRT CONTEST

Cowboy Bill’s presents the 12th annual Git-R-Wet T-Shirt Contest. This over-the-top competition Features 20 of the Hottest women on the Island getting wet and wild and vying for a $1,000 first prize!

FRIDAY, OCTOBER 21, 2022

14TH ANNUAL PIRATE BASH NEW LOCATION TURTLE KRAALS

Ahoy landlubbers! The Rum Barrel pirate crew has sailed over to Turtle Kraals. Turtle Kraals, another ship in the Rum Barrel fleet, is ready to steer the 14th Annual Pirate Bash into its long lived traditions of drinking and dressing like a pirate. More than $1500 in cash and prizes for the best pirate and wench costumes.

SATURDAY, OCTOBER 22, 2022

THAT ARENA ROCK SHOW

FREE Concert at the Sunset Pier! That Arena Rock Show is the ultimate high energy tribute to "Classic" Rock N' Roll. Performing legendary rock anthems that ruled the airwaves in the 70s and 80s. Including artists like: Led Zeppelin, Aerosmith, AC/DC, Bon Jovi, Guns N Roses to name a few.  This rock show is more than just music - it’s an experience! 0 Duval Street - 6pm

THE SIXTH ANNUAL SMALLEST PARADE IN THE UNIVERSE

WE WANT YOU! To design and build a float for the SIXTH Annual SMALLEST Parade in the Universe The 2022 THEME: The SMALLEST Parade in the Universe is a fundraiser for MARC, the Monroe Association for ReMARCable Citizens and is an official Fantasy Fest event for 2022. The Parade will take place on October 22 7PM at the Studios of Key West.

ROOFTOP CAFE’S PARADE NIGHT PARTY

It’s the best of Fantasy Fest fun in an upscale atmosphere. Come enjoy prime parade viewing from the comfort of our second-level patio. This year’s party will feature a beautiful gourmet buffet and will include beer, wine and well drinks

DAY OF THE DEAD DANCE PARTY

Come join the living dead as we dance the night away in the heart of Duval at the Old Town Rodeo with DJ Jeff! Three bars, an undead mechanical bull and incredible drink specials! Best Zombie costume contest with prizes galore at midnight! Old Town Rodeo - 618 Duval St. 8pm - 3am.

SUNDAY, OCTOBER 23, 2022

AFTER CHURCH POOL PARTY @ ISLAND HOUSE FOR MEN

The big daddy of clothing optional pool parties has been bringing boys to the yard for over 12 years! Jump into crazy fun with the Island House pool boys, loads of free shots, and a Sunday raffle that's sure to wet your whistle!

SHOKTOBERFEST AT ISLAND FARM

All you zombie-riders must bike to Cow Key where beer-loving ghouls are taking over Island Farm. Zombies are loose in the biergarten. Vampires have taken over the Lost Beach. Werewolves are cooking up brats and witches are serving cold brews. Caffeine Carl takes the stage at 6pm to feed these beasts his magical tunes. Special beers and beer specials all night.

KICK OFF ‘FANTASY FEST’ 2022 PARTY, BODY PAINT SWEEPSTAKES, & BEARD COMPETITION WITH CAPT RON WOLE

Capt. Ron Wolek is celebrating the return of Fantasy Fest at the Hard Rock Cafe Key West Kick Off Party with a Body Painting Showcase at 313 Duval Street from 6:00-8:00pm with painted models on display.

MONDAY, OCTOBER 24, 2022

MILITARY MONDAY AT IRISH KEVIN'S

Join us at Irish Kevins all day and all night on MONDAY, October 25th as we raise money to donate to The Key West Military Affairs Committee. Dress up in your best military outfit and come sip on some American Born Whiskey or Dulce Vida Organic Tequila with $1 from any of those brands of drinks going to the committee!

THE PERRY HOTEL & MARINA'S DUCK, DUCK, BOOZE POOL PARTY

Don’t miss the duckie takeover at The Perry Hotel! We’re kicking off Fantasy Fest with a pool party like you’ve never seen before – complete with a pool full of rubber duckies, beverage samples, swag, and live music by Key West’s favorite DJ Buggy. Duck floats, duckie bathing suits, duckie tutus, and creativity are encouraged!

HEROES AND VILLAINS RUN/WALK 5K

Be SUPER, be EVIL, be AWESOME and get your run on! Dress up as your favorite Superhero or Super Villain and run, walk or fly to the finish line. The first 400 to register get a custom designed puzzle piece finisher medal! Race starts and finishes near the beach at the Southernmost Beach Resort parking lot, behind the La Mer House at 506 South street Fest family friendly FUN!

MARTINI MONDAY AT VIRGILIO'S

The Original MARTINI MONDAY is rocking the Fest. All Martinis are just $7.00. Live music, great food and, of course, did I mention, the best Martinis in Key West. Have a great Fantasy Fest everyone and we will see you there! GET EXCITED BABY! Virgilio's 524 Duval St.

KINKY CARNIVAL

Key West’s Original Fantasy Fest Kink Party in its 24th year! Ticket includes: 3 hour Open Bar from 8pm – 11pm, but the party goes until 1am! Interactive BDSM stations, Fetish rooms, Bondage and more!

SLOPPY JOE’S COMIC BOOK CAPE-ERS

Come dressed as your favorite “Caped” Superhero or Supervillain and party all night. Live music on stage all day! Dancing starts at 5:30pm, Whiskey Kiss on stage at 10:00 PM, plus our house DJ will keep you dancing all night. Party starts at 8PM. No contest this year. Sloppy Joe's 201 Duval Street.

TOPS OR BOTTOMS UNDERWEAR PARTY

Underwear party 10pm-4am. Men Only Event. In the New Orleans House Garden & Pool.

TUESDAY, OCTOBER 25, 2022

DANTE'S 4TH OF JULY PARTY!

Stars and Stripes rule the day! Celebrate in your best most Patriotic Pool wear, make Uncle Sam and Betsy Ross jealous! Float and Frolic with Friends! Fantastic Food and Drink Specials from 11am to 5pm.

ELECTRO LASER NIGHT POOL PARTY AT SOUTHERNMOST BEACH RESORT

What a way to kick off your 2022 Fantasy Fest! DJ Aaron Moore and Key West Lasers will put on a show that you won't forget. Dress in your favorite rave gear and get ready to dance the night away, under the stars and synced lasers! Tuesday,10/25, 7-10pm.

ROCK THE TATAS CONTEST

Hanks’ Hair of the Dog Saloon presents Rock the Tatas Contest. Join us in the fight against Breast Cancer October 26th. Contest starts at 7 PM at Hanks Hair of the Dog Saloon located at 409 Caroline St. First place prize $500!

CAPT. TONY'S PARTY IN PLAID

Experience a party that caters to all exotic lifestyles and fantasies. Whether you wear your naughty or nice plaid to attract old friends or to stimulate the new, this party is for you. Everyone is invited to this party for the ages that only the legendary Capt. Tony's can host. Great music and drinks, plaid costumes, exotic people.

WEDNESDAY, OCTOBER 26, 2022

LIVING ON THE EDGE POOL PARTY AT OCEANS EDGE RESORT AND MARINA!

If you’re not living on the edge, you’re taking up too much space! Take a trip uptown and party down with Key West’s favorite cover band, the DurtBags, at Oceans Edge Resort’s first Fantasy Fest Pool Party! Our bartenders will be mixing up Dulce Vida tequila drink specials, and games such as cornhole and connect four will be stationed poolside. Dress or undress for your favorite decade, as we jam out to the classics through today!

SPLASH DANCE AT THE MARKER!

PATRICK & THE SWAYZEES!!!! Join us poolside for the party of the week! Bring your favorite swimsuit and cool off in one of our amazing pools while you rock out to the eclectic music performance Wednesday, 10/27, 1-4pm The Marker Key West Harbor Resort, 200 William St. 1-4pm FREE!

HUMPDAY POOL PARTY @ ISLAND HOUSE FOR MEN

What's better than a big gay pool party on Humpday? Answer: Half-Price Drinks! The men of Island House put out the best happy hour on the planet, all while providing five-star, zero dress code, stripped down debauchery. Happy hour prices from 5 - 8pm. Come experience "The Best Gay Resort In The World" as they put the hump in your humpday!

HARRIET POTTER AND THE ENCHANTED TASSEL: A BURLESQUE PARODY

Ready your wands and study your spells! It’s time to enter the wizarding world of Harriette Potter and the Enchanted Tassel: A Burlesque Parody. Whether you’re Gryffindor, Ravenclaw, Hufflepuff, or Slytherin, this sexy and saucy show is sure to have you on the edge of your Nimbus 2000 as you join Auntie Harriett Potter on a salacious search for a magical, missing tassel.

SMOKIN TUNA HOMEMADE BIKINI CONTEST

The Smokin’ Tuna Saloon is proud to present the 29th Anniversary of the Original Key West Homemade Bikini Contest. 7-8pm VIP MEET AND GREET; 8PM CONTEST Over $2,000 in cash & prizes.

WHARFSTOCK AT THE SCHOONER WHARF BAR

Travel back in time to the '60s, with Peace and Love Woodstock-style!. Feel the vibe with tie dye, flower power, and psychedelic colors in Schooner Wharf’s time capsule of the era. The sit-in starts at 7 PM.

9TH ANNUAL LUV2GLOW PARTY

Do you love to GLOW in the dark? Do you love to dance? LUV 2 GLOW is back for it's 9th annual GLOW in the dark dance party! We are very excited to be taking over the spacious, open air club located at Rick's upstairs! Come experience Rick's in a new GLOWING light and vibe like you never have before with glowing surprises and fun all night!. Featuring DJ's Jevne, Top Jimmy and Herb Javier. House music all night long, bumping electronic beats to move your glowing feet! Paint yourself up, wear your best glowing costume, blinky and LED lights welcomed, you are all the glowing stars of the party!

FOGARTY'S RED PARTY

Prepare to see RED! RED decorations, RED lights, RED drinks, and RED beach balls. Wear as much or as little RED as you want but be sure to enter the annual costume party.

DESIRE MALE FETISH PARTY

See the Little Black Book at the top of the page for full event details. Fetish Party 10pm-4am.

THURSDAY, OCTOBER 27, 2022

NAUGHTY BIKE RIDE

Come enjoy your Duval bike ride with a group of your Naughty Friends! Come get body painted; enjoy libations, titillating music and meet new friends! This is going to be a naughty ride for everyone. Registration for bikes will be online and tickets will be limited. Come ride our provided Bikes or if your and your honey want a PediCab to do all the work, they will be on hand also! 11:00 am – 1:00 pm.

SOUTHERNMOST SCAVENGER HUNT'S SECOND ANNUAL FANTASY FEST BAR CRAWL

Come one, come all and do the ONLY Fantasy Fest Bar Crawl! Grab your teams of up to 5 people to see if you have what it takes to bring home the Grand First Place Prize!

DANTE'S 15TH ANNUAL HALOS & HORNS POOL PARTY

Whether you wear the halo of an ANGEL or prefer devilish HORNS, GET WET & WILD at Dante's for a chance to win BIG $$$! Free body painting, live music, great giveaways, fantastic food, drink specials and our one of a kind stage in the CENTER of the POOL! The party starts at noon and goes till 6 PM, pole dancing starts at 4:30 PM

HARRIET POTTER AND THE ENCHANTED TASSEL: A BURLESQUE PARODY

Ready your wands and study your spells! It’s time to enter the wizarding world of Harriette Potter and the Enchanted tassel: A Burlesque Parody. Whether you’re Gryffindor, Ravenclaw, Hufflepuff, or Slytherin, this sexy and saucy show is sure to have you on the edge of your Nimbus 2000 as you join Auntie Harriett Potter on a salacious search for a magical, missing tassel.

6th ANNUAL WHITE PARTY

Come join the biggest party on the island at the 6th Annual White Party. We have something for every mood. Featuring DJs in two different venues to keep the party moving. The island’s best live rock band, The DurtBags, rocking the night away in Durty Harry's. Enjoy your secret fantasies with the lovely ladies of the Red Garter. Let your artistic side glow under the black lights. Doors open 8 PM, 202 Duval St.

PATRICK & THE SWAYZEES LIVE FROM THE LAWN AT SLOPPY JOE’S DOCKSIDE

LIVE FROM THE LAWN featuring Patrick & the Swayzees!! From surf rock to doo wop, rockabilly to beach music, Patrick & The Swayzees have created a current, yet still wholly nostalgic blend of early rock ‘n’ roll sounds that bring crowds to their feet from opening to encore. Their sets include original songs and instrumentals as well as a mix of well-known, crowd favorite cover tunes, so there’s something for everyone. Enjoy a concert under the stars, complete with beverage service from our dockside bar, Sloppy Joe's Dockside. Free to the Public!

SLOPPY JOE'S 42nd ANNUAL TOGA PARTY

Sloppy Joe’s Toga Party is “An ORIGINAL Fantasy Fest Event.” Get your toga ON and find out why we are “Still The Best Toga Party in Town!” Wear a traditional ancient Toga or dare to create your Toga using Fantasy Fest theme “All A Daze for a Holiday” Limited Toga sheets are available for purchase in the Sloppy Joe’s Retail Store for $10 (Proceeds to AH of Monroe County ). Live music on stage all day! Dancing starts at 5:30pm, Naked Karate Girls at 10:00pm, plus our house DJ make the party happen all night long. Party starts at 8PM.

FAT TUESDAY PINK PARTY

PARTY LIKE A FLOCK STAR! Wear your sexiest pink costume or pink body paint to the best Thursday night party for over a decade. Featuring limited edition Flocking Fabulous Rosé Daiquiris, live entertainment with DJ Gyver and party favors while supplies last. 305 DUVAL STREET | THURSDAY 10/28; 9 PM - CLOSE

EXPOSED AT THE BOURBON ST. PUB ADULT ENTERTAINMENT COMPLEX 9PM-4AM

See the Little Black Book at the top of the page for full event details. 10pm-4am Event Open to All! The most risqué party of Fantasy Fest! Play in the Poolside Foam Party! Dance the night away on 2 Dance Floors or Splash around in our Pool & Jacuzzi! Black Out & Black Light party inside with FREE glow sticks!

IRISH KEVIN'S ANNUAL 80's PARTY

If you love rock and roll as much as we do, come bust a move at Irish Kevin's annual 80's party! Prepare your leg warmers and Members Only jackets. Dress head to toe in your best 80's costume with awards given throughout the day. 211 Duval St.

FRIDAY, OCTOBER 28, 2022

BOWTIES & BIRTHDAY SUITS

The title says it all! Island House Resort for Men, “The Best Gay Resort in the World", invites all of you boyz for an EPIC all-male, clothing-optional pool party! All body types welcome and absolutely NO costumes needed! Mingle and frolic with other like-minded men during this daytime event! Admission includes Bowtie and free resort privileges until 4 AM Saturday. Great music, videos, go-go boys, and loads of free shots. Poolside Café and Bar open 24hrs!

DAY AT SOUTHERNMOST PLAYBOY MANSION - BEACH BUNNY POOL PARTY BASH

We invite you to join us at The Southernmost House Friday, October 29th - Noon to 5PM For the HOTTEST, MOST GLAM OCEANFRONT, ADULT ONLY, PLAYBOY BUNNY INFINITI POOL PARTY!!! 1400 Duval Street NOON-5PM

SAN CARLOS INSTITUTE LOBBY PARTY

Brave the Haunted Hallway as you make your way to the San Carlos lobby party. Mojitos Bar, Cuban Music Fest and dancing for those who are strong of heart! Noon - Midnight! 516 Duval St

OFFICIAL FLORIDA KEYS COUNCIL OF THE ARTS FANTASY FEST POSTER SIGNING PARTY

Come meet the winning 2022 Fantasy Fest poster designer Carrie Disrud and get your poster signed! As an added bonus our 2020 poster designer Pashur will also be present to sign his winning poster. WINO at the La Concha Hotel from 3 - 5pm.

21st ANNUAL LIVING ART EXPO

A showcase of the human form as a living canvas. Contestant entries are open to Female, Male or Group models competing for the title of Best Overall Living Art of Fantasy Fest 2022 and $3000 in cash and prizes. Best Overall wins $1000 in cash. FREE General Admission event.

KINKY COUPLES PARTY HOSTED BY RUBBERDOLL!

See the Little Black Book at the top of the page for full event details.

KINKY COUPLES PARTY HOSTED BY RUBBERDOLL!

See the Little Black Book at the top of the page for full event details.10:30 PM - 4 AM; 801 Bourbon Bar 

ROCKHOUSE LIVE PRESENTS THE INAUGURAL ROCK-N-ROLL FANTASY AND COSTUME CONTEST

RockHouse Live Key West is the newest and most exciting destination in Key West, featuring two amazing floors with live music, titillating cocktails, a unique rock-n-roll vibe with a Key West twist, and the biggest and best outdoor roof deck on Duval – overlooking the iconic corner of Duval & Greene, in the center of it all! Everyone has a Rock-n-Roll Fantasy, and on this night, RHL brings your rock god or goddess fantasies to life! Come dressed as your favorite rock star (or groupie) from any era and realize your Fantasy!

SATURDAY, OCTOBER 29, 2022

BOURBON ST. PUB POOL PARTY

Soaking Wet Pool Party-- Come splash around in the pool or jacuzzi while listing to music to get you hyped with live DJ and pool games. From Noon until 5pm at Bourbon St. Pub! Clothing Optional.

SAN CARLOS INSTITUTE LOBBY PARTY

Brave the Haunted Hallway as you make your way to the San Carlos lobby party. Mojitos Bar, Cuban Music Fest and dancing for those who are strong of heart! Noon - Midnight!

!SUENALO! LIVE ON THE BEACH AT SOUTHERNMOST RESORT

TOES IN THE SAND & LIVE ON THE BEACH featuring SUÉNALO, an amazing, 7-piece Latin funk band from Miami. Named by the Miami New Times as one of Miami's "Best Latin Rock Bands of All Time!" Live from the Sand Bar.

FANTASY FEST BAR MASQUERADE

All a Daze for a Holiday! Pick up a Cocktail Passport and Show off your Costumes as you travel at your own pace between bars for this Fantastical Cocktail Tour! Masquerade through Old Town Key West in your Best Fantasy Fest Theme Costume! Each Stop will include a Sample Signature Cocktail or Specialty Shot! Check in at Conch Republic Seafood Company begins at 4:00 PM; from 5pm to 8pm.

SSP GIRLS ROCK!

All the talented ladies that sing at Sunset Pier will hit the big stage for a special concert performance! In support of Mote Marine Lab, portion of the proceeds benefit Florida's Coral Reef 5:30 - 9pm Free Admission

JAM PONY DANCE PARTY AND COSTUME CONTEST

The Jam Pony Dance Party and Costume Contest! Come dance to DJ Foss and enter “best” costume contest for cash prizes! Great drink specials, Cool AC. 8pm - 2am Contest Begins at Midnight! 618 Duval St.

ROCKHOUSE LIVE PRESENTS THE INAUGURAL CLASSIC MTV PARTY

RockHouse Live Key West is the newest and most exciting destination in Key West, featuring two amazing floors with live music, titillating cocktails, a unique rock-n-roll vibe with a Key West twist, and the biggest and best outdoor roof deck on Duval – overlooking the iconic corner of Duval & Greene, in the center of it all! MTV has left an indelible imprint on most of us, from a time when they actually played music videos! We call this the “Classic Era” of MTV and hope you will come and celebrate it with us! RockHouse Live will have live music starting at opening and will run all day on both of our amazing floors AND our rooftop deck, and at 10:30pm our main ROCK band takes the stage to take you back to a time of big guitars

SUNDAY, OCTOBER 30, 2022

CHILDREN'S DAY AT ISLAND FARM Presented by Island Farm and Historic Tours of America

A family event featuring food, games, music, pony rides, archery, arts and crafts, and face painting located on Island Farm at the end of 5th Street on Stock Island. Noon to 5PM

HANGOVER REHAB POOL PARTY AT THE MARKER

Feeling hungover after your long week of debauchery? Dulce Vida Tequila and Booze Bandage to the rescue! We'll have plenty of food and drink specials, live music, along with free Booze Bandages for the first 50 guests, to bring you back to life! Sunday, 10/30, 2-5pm The Marker Key West Harbor Resort

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