Creatively Costume yourselves at all times at Fantasy Fest Events! »

2022 Schedule of Events


Creatively Costume yourselves at all times at Fantasy Fest Events!

Schedule is subject to change and will be updated as our event partners update their event details with us for 2022.

2022 Daily Diversions

FACES OF FANTASY FEST BY TOM FLIP
Key West photographer Tom Flip will be taking portraits of Fantasy Fest patrons this year from Tuesday-Friday, October 20-23. Perhaps best known for his Heads Up Key West series where he focused on the faces of Key West locals; this time, he aims to shed light on those taking part in the week-long celebration of fun by assembling a professional portrait studio. Subjects are encouraged to wear their best costumes—minimal or grandiose—to get their official Fantasy Fest portrait taken. Although this event is free and open to the public, those wishing to participate are encouraged to arrive early as lines often form and are known to stretch around the block.

FAIRVILLA THE BEST PLACE IN TOWN FOR SEXY, FUN COSTUMES & ACCESSORIES
Come to Fairvilla Sexy Things and get everything you need to look and feel your best at this year’s Fantasy Fest. Fairvilla offers a wide variety of costumes, wigs, accessories, and everything in between. Fairvilla is open daily from 11 AM- Midnight and is located at 524 Front St.

FANTASTIC BODY PAINTING AND STUNNING SUNSETS: FEMME FATALE QUATRE BODY ART AT SUNSET PIER
Join our premier all girl team of body artists Femme Fatale Quatre Body Art, October 22-30 starting each day at 1 PM at Sunset Pier, 0 Duval Street. Our talented team has won many Fantasy Fest contests with their living art pieces and we want to make you our next canvas! From small body art pieces to full body’s we can help your imaginations run wild! Now booking appointments! Call or text 850-596-4065. Walkups available on most days! Prices start at $40 and up, see our Facebook page Femme Fatale Quatre Body Art for a full price listing. We will also have waterproof and sweat proof options available as well as a bling bar for all of you glitter junkies! Come join us at Sunset Pier for fantastic body art, sunsets, music, fun and food!! 0 Duval Street Sunset Pier

FANTASY FAÇADE COMPETITION sponsored by REDDY ICE AND THE KEY WEST CHAMBER OF COMMERCE
Festively decorated homes and businesses compete for cold hard cash! Free to enter, call 305-295-9112. Entry form available HERE

FURY WATER ADVENTURES DISCOUNT
We are offering 10% off select day trips with promo code is FANTASY. Trips include: Parasail, Jet Ski Tour, Glass Bottom Boat Reef Eco Tour, Reef & Ritas Snorkel, Double Dip, Dolphin Watch, and Island Adventure. *Not valid with any other offer. One coupon per group. Blackouts and restrictions may apply.

HAIR OF THE DOG AT ISLAND DOGS
So, it's the morning after and last night's shenanigans are a bit fuzzy? Well, take the walk of shame over to Island Dogs and soak up that hangover with our Sausage Biscuits and Gravy or try our Breakfast Pizza! Get your Fantasy Fest back on by renewing yourself daily with our bottomless mimosas every day from 10am-1pm. Island Dogs 505 Front Street 305-509-7136

JIMMY BUFFET'S - ESCAPE TO MARGARITAVILLE
Jimmy Buffet's Escape to Margaritaville - The Musical. Live on Stage- This madcap love story, with an erupting volcano, tap dancing zombies and Buffett classics like Cheeseburger in Paradise, Margaritaville, It’s Five O’Clock Somewhere and Son of Sailor will fill the air on Mallory Square. - October 20 through November 12, 2022! Show starts at 8PM Click here and buy your tickets today! Waterfront Playhouse; 310 Wall St. 305-294-5015.

SUNSET HAPPY HOUR WITH CAPTAIN MORGAN COCKTAILS AT THE OPAL RESORT
Join us from 5pm to 8pm at Opal Resort for our special Captain Morgan Cocktail -SHIPWRECK PUNCH -Captain Morgan Spiced Rum, Pineapple Juice, Cranberry Juice. Served in a Fantasy Fest Festival Cup - $9 includes the cup and $8 refills. Opal Resort, 245 Front St.

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Friday, October 21, 2022

BAHAMA VILLAGE GOOMBAY FESTIVAL- A FAMILY FRIENDLY EVENT
This exuberant street party showcases island arts and crafts, music and food in the heart of Key West’s historic Bahama Village neighborhood. The festival’s main entertainment stage is located at the corner of Petronia and Front Street and features nonstop musical entertainment ranging from gospel to reggae. This is a family friendly event. Noon to midnight; FREE.

ROYAL CORONATION
Enjoy a party with the Key West's Royal Family and cast your vote for the King & Queen of Fantasy Fest! This fabulous 2-hour stage show includes entertainment by local celebrities and the Candidates themselves! Tickets include reserved seating and 3-course plated dinner. Ticket includes two votes for the Candidates of your choice. Cash bar. This evening is hosted at Key West's Truman Waterfront Park Amphitheater! Click here and get your tickets today. For more info call 305-295-9112. This is a benefit for AH of Monroe, Inc.

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Saturday, October 22, 2022

BAHAMA VILLAGE GOOMBAY FESTIVAL- A FAMILY FRIENDLY EVENT
This exuberant street party showcases island arts and crafts, music and food in the heart of Key West’s historic Bahama Village neighborhood. The festival’s main entertainment stage is located at the corner of Petronia and Fort Street and features nonstop musical entertainment ranging from gospel to reggae. This family friendly street party continues on Saturday! Noon to midnight; FREE.

THE SEVENTH ANNUAL SMALLEST PARADE IN THE UNIVERSE
WE WANT YOU! To design and build a float for the 7th Annual SMALLEST Parade in the Universe The 2022 THEME is: Cult Classics and Cartoon Chaos. 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. All floats are auctioned off at the end of the Parade in a live auction. Tickets on sale soon!

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Monday, October 24, 2022

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! This event is FREE and open to the public, 12pm-4pm. The Perry Hotel & Marina's Village Pool, 7011 Shrimp Road, 877-496-8712.

A GREEN PARROT BEATLES TRIBUTE
Well, Love, and Tony Baltimore, Chris Thomas, Hiram Garzaro, and Oren Polak, as they kick off Fantasy Week and re-create a Fab Four Show with "THE BEATLE BAND, All You Need is Love" at The Green Parrot with shows at 5:30 and 9 and 11 p.m. on Monday, October 24th. Their past Beatle Tribute Shows had Parrot patrons swinging from the rafters as they danced, laughed, and sang-along to a set-list pulled from decades of Lennon-McCartny hits. And, lets not forget "It Was Fifty Years Ago Today...." so help us celebrate the 53rd anniversary of most famous and influential rock 'n' roll record ever made, Sgt. Pepper's Lonely Hearts Club Band! Tony and the boys will hit all the high-notes of the Beatles canon, from "All My Loving" to "The Ballad of John and Yoko", through Revolver/Rubber Soul territory to The White Album. Don't miss a beat! Be there as Billy Shears gets introduced and the British Invasion roars ashore! Those on Fantasy Fest's more interactive side may want to turn this into a Monday night "Sixties Dress-Up" dance party" , come as your favorite "Beatles Look-Alike" or come dressed in theme and help turn The Parrot into the 1967 summer of love! 601 Whitehead St. 305-294-6133

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. (You can also see it behind the Southernmost Beach Cafe.) The race course goes through historic Old Town Key West. Free beer and snacks after the race. Be part of the Fantasy Fest family friendly FUN! Register HERE; Southernmost Beach Resort parking lot, behind the La Mer House at 506 South Street 6PM. Extended Happy Hour all night long at Southernmost for runners; ½ off appetizers and $5 Beer, House Wine, and Well Drinks

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! Tickets go on sale Friday – Sunday, October 22nd -24th, 12-9pm at First Flight, 301 Whitehead Street. No Pre-sales. $50, Cash Only. No Kinky Costume, No Entry.

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. Giveaways 8:00 pm - Midnight. 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 Bar; 305-293-9800; 724 Duval St.; Bourbonstpub.com

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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. Dante's Restaurant and Raw Bar, 951 Caroline St., 305-293-5123.

SOUTHERNMOST SCAVENGER HUNT'S 3rd ANNUAL FANTASY FEST BAR CRAWL
Come one, come all and do the 3rd Annual Fantasy Fest Bar Crawl sponsored by Dulce Vida Organic Tequila! Grab your teams of up 6 people to see if you have what it takes to bring home the Grand First Place Prize! There will be prizes awarded to the TOP FIVE teams. Prizes include: 2022 Fantasy Fest swag, Dulce Vida Tequila and Dulce Vida Tequila swag, shirts, coozies, free bar tabs, restaurant tabs, and much, much more! You have to WIN FIRST PLACE to find out what the GRAND PRIZE is! From the world famous Sloppy Joe's to favorite local hideouts, you will enjoy the nightlife, visit the hotspots, and maybe even learn a thing or two about our unique island paradise. Earn the most points for your team and the reward is yours! There will be prizes awarded for the BEST DRESSED TEAM! Must be 21 or older and you do not have to drink to participate. $45 per person includes the activity, the free drink, the exclusive map with a value of over $160 and if you win you'll get a lot more! The bar crawl check in is at 2:00pm. The hunt begins at 2:30pm and ends at 4:30pm with award and winners announced at 5:00 pm. Buy tickets HERE

COCKTAILS FOR ANIMAL TAILS!
COCKTAILS FOR ANIMAL TAILS! LOCATION: Rick's Complex, 202 Duval St. 305-294-4857 TIME: 7-10 PM Admission $40- All you can DRINK Come to an official charity event to benefit the homeless animals of the Florida Keys SPCA. It’s an “All You Can Drink” Animal Party where each bar has been transformed into a different Animal Kingdom around the world where you will enjoy an unlimited drink experience of the entire Rick’s Complex. Wear your best animal ears & tails, warm up your tutus and get ready to party like an animal! Join in the costume contest to win a $500 grand prize! Proceeds will benefit the animals of the Florida Keys SPCA. Pre-sale tickets are available at Flkspca.org. . Questions call 305-294-4857.

SHE-AVENGERS STRIPFINITY WARS: A BURLESQUE PARODY
In a different dimension of the multiverse, the salacious stripping superhero's known as the She-Avengers, unite to defeat their most powerful enemy yet! Fanos, a madwomen with plans to to impose her twisted will on the universe, sets her sights on collecting artifacts of unlimited power, the Stripfinity Stones. These stones have the power to create or destroy everything sexy in the universe. The She-Avengers must enlist the help of the Garters of the Galaxy, a group bump and grind bad-asses, to collect and protect the stones at all cost in this bawdy burlesque parody featuring all of your favorite Key West Burlesque performers. Location - Key West Theater 512 Eaton Street Doors -7pm Show - 8pm Tickets - $55-$125 per person Tickets available online at thekeywesttheater.com.

TUTU TUESDAY RETURNS!
Tutu Tuesday is back!! Come in your favorite tutu themed costume. We will be celebrating the glory of the TuTu and all of its wonderment! Dance Party with Jevne + Multiple DJ's, Get Tickets Now $22 Available only at 22&Co, Entrance at 504 Angela Street, Online sales start October 1st, Doors open at 7 PM, No Tutu No Entry!

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. 428 Greene St. 305-294-1838. 8 PM; FREE.

GREEN PARROT GREEN PARTY “It’s Not Easy Being Green!”
As once said by a famous frog - “it’s not easy being green!” But we’re not frogs, were The Parrot, and day-in and day-out, we happily recycle our bottles, cups, and cans, and invite you on this night to rethink and reinvent yourself, maybe take your recyclables and reinvent a radical costume...or heck, just wear green...we won’t throw you out! Be here as Gainesville-based Tom Petty tribute band Heavy Petty makes their much-anticipated debut at The Green Parrot with shows at 5:30, 10 p.m and midnight. on Tuesday, October 25th. Heavy Petty grew up in the culture, music, and community of Tom Petty’s hometown, Gainesville, FL, cultivated in the same rock and roll scene where Tom Petty grew up. Known for their energy, showmanship, authenticity, and their own Gainesville-grown rock and roll style, they were dubbed the “Hometown Tribute Band” by friends and family of Tom Petty, and have been carrying on Tom Petty’s music legacy and entertaining large audiences for ten years. 601 Whitehead Street 305-294-6133

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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! Havana Nights Pig Roast for lunch, includes Cuban pork, rice and beans, and plantains for $25 plus tax and gratuity. This will be served at the pool party on the pool deck. This a 21+ Event. FREE ADMISSION 12-3PM at Oceans Edge Resort and Marina 5950 Peninsular Ave, Stock Island, Florida 33040

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 pool party realness! Happy hour prices from 5 - 8pm. Come experience "The Best Gay Resort In The World" as they put the hump in your humpday! Poolside Café is open 24hrs! $50 cash/credit at the door. Photo ID required. MEN ONLY. Admission includes lock & locker, pool towels, and resort membership until Thursday @ 4am. 1129 Fleming St., Call 305-294-6284 for information.

PET MASQUERADE
New time!!!!! The Pet Masquerade is excited to announce that you will see this year’s carousel of frisky pets and playful owners performing for fame, fortune and prizes beginning at 6:30p on the stage of the Key West Amphitheater at the Truman Waterfront Park! Think you and your furry, feathered or slithery friend have the perfect outfit? 4 categories to enter including Junior-$25 each entry; benefits the Lower Keys Friends of Animals; Registration begins at 5 PM; Show starts at 6:30 PM; FREE to watch, plenty of FREE seats available or bring your blanket and lawn chair. NO COOLERS. Food and beverage available on site. 21 E. Quay Rd. For more information, visit our Facebook Page or email [email protected].

SHE-AVENGERS STRIPFINITY WARS: A BURLESQUE PARODY
In a different dimension of the multiverse, the salacious stripping superhero's known as the She-Avengers, unite to defeat their most powerful enemy yet! Fanos, a madwomen with plans to to impose her twisted will on the universe, sets her sights on collecting artifacts of unlimited power, the Stripfinity Stones. These stones have the power to create or destroy everything sexy in the universe. The She-Avengers must enlist the help of the Garters of the Galaxy, a group bump and grind bad-asses, to collect and protect the stones at all cost in this bawdy burlesque parody featuring all of your favorite Key West Burlesque performers. Location - Key West Theater 512 Eaton Street Doors -7pm Show - 8pm Tickets - $55-$125 per person Tickets available online at thekeywesttheater.com.

SMOKIN TUNA HOMEMADE BIKINI CONTEST
The Smokin’ Tuna Saloon is proud to present the 29th Anniversary of the Original Key West Homemade Bikini Contest. 8PM CONTEST Over $2,000 in cash & prizes. Creativity and attention to detail are the key elements to winning the 1st prize of $1000. Additional cash prizes for 2nd & 3rd place. Hosted by the World Famous Emcee and Local Celebrity Mr. Bill Hoebee and his celebrity judges. For contest entry ideas please see the gallery for pictures of previous years. Contest participation is $20. General Admission $20 Doors open at 7 PM, Event Starts @ 8pm. Click here and buy your general admission tickets or to purchase a table today. Click here

THAT ARENA ROCK SHOW
FREE Concert at the Sunset Pier! The ultimate high energy and theatrical tribute to "Classic" Rock & Roll. Performing legendary rock anthems that rules the airwaves in the 70's & 80's. This show will take you on a trip back in time, turning Sunset Pier into an arena a night! Get your lighters out and your fist in the air. The Rock Show is more than just music - it's an experience. 7:00PM - 9:00PM

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. Prizes for sexiest Hippie Chick and Grooviest Dude -- judging at 8:30 PM. Groove to live music and dance to tunes reaching back in time from Raven Cooper and the Hippies from 7-midnight, plus cold drinks and great galley fare. Cash prizes and gift certificates to the winners!. 202 William St.; 305-292-9520. No cover charge or entry fee to The Man.

10TH ANNUAL LUV2GLOW PARTY
Celebrating our 10th anniversary of LUV2GLOW! Fantasy Fest’s best and longest running glow in the dark dance party!! Get your glowing costumes, paint, blinky lights/LEDS and UV reactive vibes flowing. We’re back at Rick’s Upstairs! House music all night long, bumping electronic beats to move your glowing feet. DJs Jevne, Top Jimmy, Jimmy Jamz + special guest will keep everyone Glowing bright all night. NO GLOW NO ENTRY! Glowing options available at the door for non glowers. $20 Pre-Sale available at Rick’s starting Thursday 10/20/22 - Day before party, $30 at Door, Cash Only. 8PM-4AM 21+ Rick’s Upstairs 202-208 Duval St. Join us for some radical self expression. For more info follow us at facebook.com/Luv2Glow

SLOPPY JOE'S SLUMBER PARTY
Roll out of bed and head on over to Sloppy Joe’s Slumber Party. Be creative. Be goofy. But be dressed in a costume…will it be… a onesies, flannel jammies, boxers or your favorite lingerie. Create your outfit around Fantasy Fest Theme “ Cult Classics & Cartoon Chaos” (a costume you can wear all week). Spend the day/night partying and dancing in comfort at Sloppy Joe’s. Party starts at 8pm

DESIRE MALE FETISH PARTY
Fetish Party 10pm-4am. Men Only Event. In the New Orleans House Garden & Pool Bar.; 305-293-9800; 724 Duval St.; Bourbonstpub.com

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Thursday, October 27, 2022

BERKSHIRE HATHAWAY PARADE OF HOMES MEGA OPEN HOUSE EVENT
Berkshire Hathaway Keys Real Estate | Knight & Gardner Realty invites you to their PARADE OF HOMES EVENT! Stop by any of their Open Houses and enter for a chance to win an Ultimate Night on the Town Gift Basket, stuffed with gift certificates to some favorite spots in town. Visit their website for a full list of our open houses & check their Facebook page. October 27th from 11-3pm.

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 – Registration and Pre Party @ 803 Duval Street Parking lot with music provided my DJ Lucas to get you in the spirit. Open Bloody Mary & Mimosa Bar! 1:00 pm ride kicks off to Irish Kevin's with free admission. Bikes will be picked up there. Buy Tickets Here

SOUTHERNMOST SCAVENGER HUNT'S 3rd ANNUAL FANTASY FEST BAR CRAWL
Come one, come all and do the 3rd Annual Fantasy Fest Bar Crawl sponsored by Dulce Vida Organic Tequila! Grab your teams of up 6 people to see if you have what it takes to bring home the Grand First Place Prize! There will be prizes awarded to the TOP FIVE teams. Prizes include: 2022 Fantasy Fest swag, Dulce Vida Tequila and Dulce Vida Tequila swag, shirts, coozies, free bar tabs, restaurant tabs, and much, much more! You have to WIN FIRST PLACE to find out what the GRAND PRIZE is! From the world famous Sloppy Joe's to favorite local hideouts, you will enjoy the nightlife, visit the hotspots, and maybe even learn a thing or two about our unique island paradise. Earn the most points for your team and the reward is yours! There will be prizes awarded for the BEST DRESSED TEAM! Must be 21 or older and you do not have to drink to participate. $45 per person includes the activity, the free drink, the exclusive map with a value of over $160 and if you win you'll get a lot more! The bar crawl check in is at 2:00pm. The hunt begins at 2:30pm and ends at 4:30pm with award and winners announced at 5:00 pm. Buy tickets HERE

THE HEAVY PETS, LIVE ON THE BEACH AT SOUTHERNMOST BEACH RESORT
The Heavy Pets are a funked-up rock and roll band from South Florida. Called "a living, breathing force of nature" by Relix magazine, they are known for their songcraft and powerhouse live performances. The band has been a mainstay on the national touring circuit for over a decade and released its fourth full-length studio album Strawberry Mansion in February 2018. FREE! Reserve your space HERE

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; Dante's Restaurant & Raw Bar, 951 Caroline Street next to the ferry terminal. 305-293-5123. $. Visit for more details danteskeywest.com.

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! Additional cash prizes for second and third place. DJ and special performances by Rob Benton & Friends. Contest winner awarded starting at 10 PM. A portion of the proceeds benefiting Making Strides Against Breast Cancer. Doors open at 5pm, show starts at 7pm until late! Body Painting Artist on site if you want to fancy up your Tatas! Hanks Hair of the Dog Saloon 409 Caroline St. $20 Cover and $20 entry fee.

SHE-AVENGERS STRIPFINITY WARS: A BURLESQUE PARODY
In a different dimension of the multiverse, the salacious stripping superhero's known as the She-Avengers, unite to defeat their most powerful enemy yet! Fanos, a madwomen with plans to to impose her twisted will on the universe, sets her sights on collecting artifacts of unlimited power, the Stripfinity Stones. These stones have the power to create or destroy everything sexy in the universe. The She-Avengers must enlist the help of the Garters of the Galaxy, a group bump and grind bad-asses, to collect and protect the stones at all cost in this bawdy burlesque parody featuring all of your favorite Key West Burlesque performers. Location - Key West Theater 512 Eaton Street Doors -7pm Show - 8pm Tickets - $55-$125 per person Tickets available online at thekeywesttheater.com.

THAT ARENA ROCK SHOW
FREE Concert at the Sunset Pier! The ultimate high energy and theatrical tribute to "Classic" Rock & Roll. Performing legendary rock anthems that rules the airwaves in the 70's & 80's. This show will take you on a trip back in time, turning Sunset Pier into an arena a night! Get your lighters out and your fist in the air. The Rock Show is more than just music - it's an experience. 7:00PM - 9:00PM

39th ANNUAL HEADDRESS BALL
The Key West Business has had a busy year with the Headdress Ball in 2022. Our 38th annual Headdress Ball had been postponed 4 times over a two year period due to COVID-19. Some patrons had been holding tickets for 21/2 years. We decided to proceed with the event during Mardi Gras this year on February 26 and the event was very successful. However, we are delighted to be able to return to our original time under the Fantasy Fest umbrella for our 39th presentation on Thursday evening, October 27 at the Coffee Butler amphitheater at 8 PM. We also return to our original table, chair and grass seating, and tickets will be listed July 1 on www.keystix.com. See talented headdress makers compete for the First place prize of $3,000, second place of $1,000 and $500 for third, judged from the shoulders up. Eight great talent acts will be also featured. Laurie Thibaud of Aqua Idol fame returns as emcee. Bar and food service during the performance. Proceeds from the Headdress Ball go to promote LGBTQ+ tourism worldwide to Key West. Questions and Contest registration? Please go to the Key West Business Guild website or call 305-294-4603. Book early because this event always sells out.

SLOPPY JOE'S 43rd 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 “Cult Classics & Cartoon Chaos ” 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, Juliano Brother on stage at 10:00pm, plus our house DJ make the party happen all night. Party starts at 8PM. Giveaways 8:00pm to midnight. Sloppy Joe’s 201 Duval Street.

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. Costume contest with a $500 bar tab for 1st place, $250 bar tab for 2nd place and $100 bar tab for 3rd place. All cover charges will be donated to the American Cancer Society - Making Strides Against Breast Cancer of the Florida Keys. 305 DUVAL STREET | THURSDAY 10/28; 9 PM - CLOSE; $

EXPOSED AT THE BOURBON ST. PUB ADULT ENTERTAINMENT COMPLEX 9PM-4AM
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! VIP All Access Tickets $50 day of the event . (VIP All Access includes the Main Bar, Garden & Pool Bar and Foam Party) tickets will be on sale at the New Orleans House starting October 1st; open 8 AM-8 PM; General Admission Tickets $20 (Access to the Main Bar only) Tickets available the night of the event at the door. 305-293-9800; 724 Duval St.; Bourbonstpub.com

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. We have live entertainment from open to close, but at 10:30 PM our full 80's band will keep you fighting for your right to party into the wee hours of Friday morning. 211 Duval St; 305-292-1262; 10:30 PM

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Friday, October 28, 2022

BOWTIES & BIRTHDAY SUITS
BOWTIES & BIRTHDAY SUITS @ ISLAND HOUSE FOR MEN (12Noon-5pm) The title says it all! Island House Resort for Men, “The Best Gay Resort in the World", invite all of your 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 resort membership until 4 AM Saturday. Great music, videos, and friendly shot boys! Poolside Café is open 24hrs! Locks & lockers provided while they last as well as a free clothes-check. 12-5 PM. $50 cash/credit at the door. Photo ID required. MEN ONLY. Admission includes lock & locker, pool towels, and resort membership until Saturday @ 4am. 1129 Fleming St, Call 305-294-6284 for information.

DAY AT SOUTHERNMOST PLAYBOY MANSION - BEACH BUNNY POOL PARTY BASH
We invite you to join us at The Southernmost House Friday, October 28th - Noon to 5PM For the HOTTEST, MOST GLAM OCEANFRONT, ADULT ONLY, PLAYBOY BUNNY INFINITI POOL PARTY!!! Enjoy an all day pool pass, DJ Hazard, Drink Specials, and yes you can sunbathe topless as long as you wear your bunny ears. Admission: $25 1400 Duval Street, Key West 305-296-3141; NOON-5PM

RED ELVISES POOL PARTY AT THE MARKER!
Get your swimsuit and come out to party with Red Elvises! This band has produced 12 studio albums, two live albums, a live concert DVD, and a Greatest Hits compilation. Some of their most notable film contributions include music and or performances in “Six String Samurai”, “Mail Order Bride”, “Armageddon”, “Skippy”, “Melrose Place”, “Fastlane”, “Penn and Teller’s Sin City Extravaganza”, “VH-1 Behind the Music”, and “MTV. No matter where they perform, Igor & Red Elvises always bring the party with them. FREE! Reserve your space HERE

OFFICIAL FLORIDA KEYS COUNCIL OF THE ARTS FANTASY FEST POSTER SIGNING PARTY
Come meet the winning 2022 Fantasy Fest poster designer and get your Official Fantasy Fest poster signed! WINO at the La Concha Hotel from 3 - 5pm.

MASQUERADE MARCH
Join the crowd as they parade through Old Town with music and noisemakers! Thirst quenchers provided at selected guesthouses. Begins at the Old Town Wine & Spirits on Truman but revelers can join the mad march anywhere along the ONE route! Start marching at 5:30 PM; All welcome; FREE.

SHE-AVENGERS STRIPFINITY WARS: A BURLESQUE PARODY
In a different dimension of the multiverse, the salacious stripping superhero's known as the She-Avengers, unite to defeat their most powerful enemy yet! Fanos, a madwomen with plans to to impose her twisted will on the universe, sets her sights on collecting artifacts of unlimited power, the Stripfinity Stones. These stones have the power to create or destroy everything sexy in the universe. The She-Avengers must enlist the help of the Garters of the Galaxy, a group bump and grind bad-asses, to collect and protect the stones at all cost in this bawdy burlesque parody featuring all of your favorite Key West Burlesque performers. Location - Key West Theater 512 Eaton Street Doors -7pm Show - 8pm Tickets - $55-$125 per person Tickets available online at thekeywesttheater.com.

MASQUERADE MARCH AFTER-PARTY
Remember! The fun doesn’t end just because the marching does! All are invited to stay "in-costume" after you "second-line" your way to the corner of Southard and Whitehead as The Old Town Masquerade March Madness continues at 7:30 p.m. on Friday, October 28th as the Green Parrot Masquerade March After-Party keeps the ball rolling as fancifully-costumed local participants complete their free-spirited, moving-cocktail party through the streets of historic Old Town because, "sooner or later, you always wind up at The Green Parrot". 601 Whitehead Street 305-294-6133

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 $2000 in cash and prizes. Best Overall wins $1000 in cash. FREE event. New for 2022 - Front stage standing room and Sunset Pier table seating is all first come, first serve. Live DJ & MC Bill Hoebee on the Full Concert Stage with Catwalk. Party Starts at 7pm. Contest begins at 8pm. Contestant Registration - contact Sunset Pier 305-295-7047 or [email protected]

KINKY COUPLES PARTY HOSTED BY RUBBERDOLL!
The ONLY strictly Couples Only event. Join like-minded couples in the Cabaret bar overlooking Duval Street. A special performance by the world-renowned latex performer RubberDoll with Live Dark'n Dancing with New York DJ Lucas will be sure to get everyone in the mood for some serious playtime. Doors open ten minutes before showtime. Shows at 9:00pm and 11:00pm both Friday and Saturday - Check-in is at the Downstairs Bar. Private Area, Premium Open Bar, Clothes Check Couples Only! Come Together, Leave Together Re-Entry Permitted/Pre-Registration Required. NO EXTRA TICKETS WILL BE AVAILABLE WHEN THIS EVENT SELLS OUT! TICKETS CANNOT BE TRANSFERRED TO ANYONE ELSE! Friday $275 per couple/$50 Single Ladies Saturday $300 per couple/$50 Single Ladies Both Nights with Meet and Greet: $500 Contact Jim with questions (305)304-2400 Buy Tickets Here

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! Prizes will be awarded all day and night, with the big contest at midnight and a $500 cash prize to the winner (must be present to enter). 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 to your Rock Fantasy (Island – “da plane da plane!!”). Dress code: “Um, what’s a dress code?” ;). 135 Duval (corner of Greene & Duval); 305.440.3263; 10:30 PM; $100 admission to our roof top deck; $150 with reserved seating. Buy tickets HERE

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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. 724 Duval St 305-294-9354

SAN CARLOS INSTITUTE BLOCK PARTY
The San Carlos Institute is bringing back their annual Block Party! Dance the night away and enjoy - Mojitos Bar, Cuban Music Fest and dancing for those who are strong of heart! Noon - Midnight! 516 Duval St 305-294-3887 Free Entry.

GLASS CATS- LIVE ON THE BEACH AT SOUTHERNMOST RESORT
The ultimate beach & BBQ Rock & Roll party! Glass Cats has been playing their experimental jam-based, funky soul-filled grooves around town for the past couple of months, and they’re AMAZING! The four-piece band consists of Myles Mancuso on guitar and vocals, Mark King on bass and vocals, Michael Wingate on keys and vocals, and Evan Valentine on drums and vocals.10/29, 3-6pm Southernmost Beach Resort, 1319 Duval St. FREE! Reserve your space HERE

BOURBON ST. PUB'S VIP BALCONY BASH
Join us for one of the best views of the Fantasy Fest parade on Duval St. from the Grand Balcony of the New Orleans House. Don't deal with the crowds! VIP high-end open bar and catered buffet-no need to go anywhere else. Private entrance and restrooms. Free bag of beads to toss to the crowd below! MC'd by John "Ma" Evans. Don't miss this opportunity for a great vantage point to see the parade and a fantastic party. VIP Tickets $200. No reserved spaces, first come, first served. Only 150 tickets available! Tickets on sale October 1 at the New Orleans House 305-293-9800 724 Duval Street open 8 AM-8 PM or keystix.com. ; 724 Duval Street $$ doors at 6pm

PARADE VIEWING AT THE HARD ROCK CAFÉ
Join us and experience "Cult Classics & Cartoon Chaos" for the best viewing of the Fantasy Fest parade on Duval St. Hard Rock Cafe will be grilling up a Fantasy Fest exclusive menu. Priority seats still remain but we sell out early every year so let us know today! Contact Kelly at [email protected] for VIP red carpet treatment. 313 Duval Street, 305-293-0230. Doors open at 6 PM!

BUD LIGHT FANTASY FEST PARADE
Join 70,000 exuberant partygoers as this year’s Bud Light Fantasy Fest parade rolls down Duval Street. Featuring glittering floats, spectacular costumes and dazzling dancing groups! It doesn’t get any wilder than this! Parade steps off at 7 PM; FREE. Live Southernmost Point Webcam Sloppy Joe's Live Crowd Cam Live Duval Street Cam Live Irish Kevin's Cam

FANTASY FEST GRAND PARADE BALCONY VIEWING PARTY
Come join the party that will be watching the parade on the largest balcony on Duval street ! This balcony viewing party for Fantasy Fest is going to bring your past and your future into the present! Open Bar, Light Hors d’Oeuvres, beads to throw and an amazing view of the 2021 Fantasy Fest Parade. 801 Bourbon Bar - 801 Duval St.

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Sunday, October 30, 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! Remember, after church, and before Tea Dance, comes ISLAND HOUSE! Poolside Café is open 24hrs! $50 cash/credit at the door. Photo ID required. MEN ONLY. Admission includes lock & locker, pool towels, and resort membership until Monday @ 4am. 1129 Fleming St., Call 305-294-6284 for information.

CHILDREN'S DAY
A family event featuring food, rides, games, arts and crafts and a costume contest for children located at Bayview Park. Truman Ave. and Eisenhower Dr.; Noon to 5 PM; 305-292-8912.

HANGOVER REHAB POOL PARTY AT SOMO'S PINEAPPLE POOL
We'll have plenty of food and drink specials, and a live DJ spinning all your favorites, along with free Booze Bandages for the first 50 guests, to bring you back to life! Sunday, 10/30, 1-4pm Southernmost Beach Resort’s Pineapple Pool. FREE! Reserve your space HERE

REGGAE REHAB POOL PARTY AT THE MARKER w/REGGAE LOU & THE KIND BUDZ
Feeling hungover after your long week of debauchery? Captain Morgan, Ketel One Botanicals, and Booze Bandage to the rescue! We'll have plenty of food and drink specials, live music by Reggae Lou, 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, 200 William St. 2-5pm FREE! Reserve your space HERE

“THE FAT LADY SINGS” TEA DANCE
As the saying goes, “It ain’t over ‘til the fat lady sings.” Everyone will be at La Te Da from 4 PM to 8 PM for the last official event of Fantasy Fest 2020. DJ Rude Girl provides the music for the very last hoorah! La Te Da - Hotel, Restaurant, Cabaret and Bars, 1125 Duval St.; 305-296-6706; $5.

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