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2021 Schedule of Events


2021 Little Black Book Schedule »

2021 Daily Diversions

A MIXED UP MUDDLED UP SHOOK UP WORLD
The Key West Art & Historical Society is pleased to announce the opening of “A Mixed Up, Muddled Up, Shook Up World” an exhibition featuring Fantasy Fest image captured by Mark Hedden on display in the Bumpus Gallery at the Custom House Museum, 281 Front Street. Mark Hedden has been living in Key West for over 25 years and he still hasn’t figured out the city’s annual bacchanalia. A couple years ago he decided to start approaching the event through the practice of street photography, trying to take it all in with a dispassionate eye and a willingness to let unexpected narratives unfold before the camera. A lot of his work is concerned with public and private space and public and private behavior in those spaces. Fantasy Fest is an amazing petri dish for that, fueled by myriad potent catalysts, such as sexuality, gender identity, age, body type, race and politics. It’s a mix of the high and the low, the earthy, the ethereal and the cheap, and he’s created a pretty deep catalog of images from the event. The exhibition runs until November 7, 2021 and is sponsored by the Helmerich Trust and the Florida Division of Cultural Affairs.

BODY PAINTING BY CAPTAIN RON WOLEK AT Hard Rock Cafe
Get painted by Hollywood celebrity make-up artist Ron Wolek and his stellar crew! Smart to pre-book your appointment NOW with Wolek Studios’ top designers – and Wear one of ‘The Captain’s’ epic custom looks to the Fest! Plan on stealing the show with your ultra-chic edge, created only by this hair, make-up and body design artist, world-experienced in film, theater, television and entertainment.

FAIRVILLA THE BEST PLACE IN TOWN FOR SEXY, FUN COSTUMES & ACCESSORIES
Come to Fairvilla and get everything you need to look 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.

KARAOKE! AT THE JAM PONY KARAOKE CLUB
Come sing your heart out seven nights a week at the Jam Pony Karaoke Club. Open 8pm to 3am. Nightly Karaoke contests with wonderful prizes for the BEST and WORST Performers. "It's OK to sing off Key (West) at the Jam Pony!" 618 Duval St.

KEY WEST HAUNTED HALLWAYS
Thrills and chills at 618 Duval 7pm to 11 pm Adults 21 and over $15 Kids under 21 $10 Adults receive a free drink ticket Kids get a trick or treat bag

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.

THE ROCKY HORROR SHOW
The Rocky Horror Show. Starring Christopher Peterson. October 14 through 29, 2021 Live on stage! That sweet transvestite and his motley crew are back for the Time Warp and it’s better than ever baby! Click here and buy your tickets today! Waterfront Playhouse; 310 Wall St. 305-294-5015.

WORLD'S SMALLEST PARADE FLOATS
SIXTH Annual SMALLEST Parade in the Universe The 2021 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 2021. The Parade will take place on October 23 7PM at the Studios of Key West. All floats are auctioned off at the end of the Parade. BID NOW.This year we are partnering with The Studios of Key West and the floats will be exhibited for the ENTIRE month of October in the Main Gallery!

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Saturday, October 23, 2021

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 show will take you on a trip back in time, turning every sized venue into an arena for a night! Get your lighters out and your fist in the air. 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 2021 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 2021. The Parade will take place on October 23 7PM at the Studios of Key West. All floats are auctioned off at the end of the Parade. BID NOW This year we are partnering with The Studios of Key West and the floats will be exhibited for the ENTIRE month of October in the Main Gallery!

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.

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Sunday, October 24, 2021

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! $40 cash/credit at the door. Photo ID required. MEN ONLY. Admission includes lock & locker, pool towels, and resort privileges until Monday at 4am 1129 Fleming St., Call 305-294-6284 for information.

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. Cash prize for the most shocking body painting. Fire dancers. Hula Hoopers. Disco Tipis. Oh my this is going to be good fun on the farm. Bike to the end of 5th St. from Stock Island if you dare. Adults-only please. $40 advance purchase includes OktoberFEAST supper ($45 at the gate). Book now. Availability is limited. Buy tickets in advance HERE

KICK OFF ‘FANTASY FEST’ 2021 PARTY, BODY PAINT SWEEPSTAKES, & BEARD COMPETITION WITH CAPT RON WOLEK
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. All food and alcoholic drinks purchased between 6:00-8:00pm will receive a raffle ticket for the ultimate body painting prize; a FREE 5 day pass for a week’s worth of body painting with Capt. Ron’s Hollywood Body Art. There’s more! MUSTACHEPARLOR.com will host a sanctioned BEARD & MUSTACHE COMPETITION with prizes in over 12 categories, such as the build your own 'Fantasy Beard'. All genders may enter to become bearded champions. Pre-register HERE for details on each category and for pre-registration. You may also enter on-the-spot at Hard Rock Cafe Key West from 12:00-3:00pm Sunday Oct. 24th. Winners of the sweepstakes and beard competitions will be announced at 8:15pm at the end of the Hard Rock Cafe Key West Kick Off Party with Capt. Ron Wolek. Also, all advanced booking of body painting and makeup will be 50% off Sunday Oct 24th, so book your appointments NOW

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Monday, October 25, 2021

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! This event is FREE and open to the public, 12pm-4pm. The Perry Hotel & Marina's Village Pool, 7011 Shrimp Road, 305-296-1717.

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. 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 Bar; 305-293-9800; 724 Duval St.; Bourbonstpub.com

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Tuesday, October 26, 2021

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.

ELECTRO LASER NIGHT POOL PARTY AT SOUTHERNMOST BEACH RESORT
What a way to kick off your 2021 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,10/26, 7-10pm. Southernmost Beach Resort, 1319 Duval St.7-10pm FREE ENTRY! Reserve your space here

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. Location - Key West Theater 512 Eaton Street Doors -7pm Show - 8pm Tickets - $50-$125 per person Tickets available online at thekeywesttheater.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.

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.

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Wednesday, October 27, 2021

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

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! $40 cash/credit at the door. Photo ID required. MEN ONLY. Admission includes lock & locker, pool towels, and resort privileges until Thursday @ 4am. 1129 Fleming St., Call 305-294-6284 for information.

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. Location - Key West Theater 512 Eaton Street Doors -7pm Show - 8pm Tickets - $50-$125 per person Tickets are 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. 7-8pm VIP MEET AND GREET; 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. Join the Backstage VIP section @ 7pm with an open bar, appetizers and a contestant meet & greet. 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 contestants. smokintunasaloon.com Limited Backstage VIP Tickets $50 Contest participation is $20. General Admission $20 Doors open at 7 PM, Event Starts @ 8pm. Click here and buy your tickets today.

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.

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! NO GLOW NO ENTRY $20 cover at the door. INCLUDES 1 FREE Dulce Vida Cocktail. 8PM-4AM 21+ Body painter at the door for non glowers. Glow yourself up and join us for some radical self-expression!!

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. Cash, gift certificates, and/or bar tabs will be the prizes for winner!! The DJ Jimmy Jamz will keep you dancing all night long. Join us for a fun RED filled night that everyone needs and deserves! Fogarty's 227 Duval St. 305-294-7525 9 PM

DESIRE MALE FETISH PARTY
See the Little Black Book at the top of the page for full event details. 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 28, 2021

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 28th 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 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! Each participant will receive an exclusive Scavenger Hunt map featuring tons of 2-4-1 drink coupons you can use any time while you are in Key West! You will need to follow the creative clues and solve the riddles while you explore and experience the uninhibited side of Key West like never before. 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. Of course there are bonus opportunities and mystery locations to discover as well so don’t get left behind! Must be 21 or older and you do not have to drink to participate. $30 per person includes the exclusive map with a value of over $120. Starting at 4PM at The Conch Republic Seafood Company, 631 Greene St. Click here and get your tickets today.

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.

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. Location - Key West Theater 512 Eaton Street Doors -7pm show - 8pm Tickets - $50-$125 per person Tickets are available online at thekeywesttheater.com.

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! Hosted on The Perry Hotel & Marina's Village Event Lawn. 8pm 7001 Shrimp Road

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. No contest this year. Sloppy Joe's 201 Duval Street. Live Stage Cam Live Bar Cam Live Crowd Cam

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
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! 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 29, 2021

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! Locks & lockers provided while they last as well as a free clothes-check. 12-5 PM. Buy $30 tix at keystix.com or $40 at the door with cash or credit card. Men 18+ Only *PHOTO ID REQUIRED FOR ALL ENTRANTS*

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!!! 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

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 305-294-3887 Free Entry.

OFFICIAL FLORIDA KEYS COUNCIL OF THE ARTS FANTASY FEST POSTER SIGNING PARTY
Come meet the winning 2021 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. Posters and other Fantasy Fest Swag for Sale!

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. Location - Key West Theater 512 Eaton Street Doors -7pm show - 8pm Tickets - $50-$125 per person Tickets are available online at thekeywesttheater.com.

20TH 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 2021 and $3000 in cash and prizes. Best Overall wins $1000 in cash. FREE General Admission event. VIP Backstage and Stage-front tickets available at keystix.com . Doors open at 7 PM; Contest starts at 8 PM; For entry information contact the Sunset Pier 305-295-7047 or [email protected].

KINKY COUPLES PARTY HOSTED BY RUBBERDOLL!
See the Little Black Book at the top of the page for full event details. 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; $150 with reserved seating. Buy tickets HERE

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Saturday, October 30, 2021

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 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 305-294-3887 Free Entry.

!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. Cash bar featuring Froze and Sangria by Cupcake Wines and Beso Del Sol and assorted beer, wine and spirits. Saturday, 10/30, 1-4pm Southernmost Beach Resort, 1319 Duval St, 1-4pm $25 - $60 Tickets available here

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! Buy your tickets in advance HERE Check in at Conch Republic Seafood Company begins at 4:00 PM; Stroll and Show Off your costume from 5pm to 8pm. Presented by Dulce Vida Tequila & Captain Morgan Rum. First 200 to Check In will receive a FREE Fantasy Fest Vintage T-shirt (T's from our 2017-2019 Festivals - quantities and sizes are limited and Based on Availability)

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.

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 - 801 Duval St. Buy Tickets Here

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, Aquanet, and short skirts (skirts not required, stilettos recommended ;). 135 Duval (corner of Greene & Duval); 305.440.3263; 10:30 PM; $100 admission; $150 with reserved seating. Buy tickets HERE

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Sunday, October 31, 2021

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; 305-292-8912 for information.

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, 10/31, 2-5pm The Marker Key West Harbor Resort, 200 William St. 2-5pm FREE! Reserve your space here

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