You are here

Fantasy Fest 2021

10/22/2021 - 12:00am to 10/31/2021 - 12:00am

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!

Events are being added/deleted due to COVID - please see their website for full and UPDATED schedule.

MONDAY, OCTOBER 25, 2021

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.

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. $60, 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. No door charge. Sloppy Joe's 201 Duval Street.

TOPS OR BOTTOMS
See the Little Black Book at the top of the page for full event details. Underwear party 10pm-4am. Men Only Event. In the New Orleans House Garden & Pool Bar; 305-293-9800; 724 Duval St.

TUESDAY, OCTOBER 26, 2021

Harriette 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 onsite 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.

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. You can’t help yourself from fallin’ for our premier guest body painter, Rock Star Airbrush! Dress or undress for your favorite decade, as we jam out to the classics through today! This a 21+ Event. FREE ADMISSION 12-3PM at Oceans Edge Resort and Marina 5950 Peninsular Ave, Stock Island, Florida 33040

Harriette 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. It’s tie-dye, flower power, and psychedelic colors in a time capsule of the era at Schooner Wharf Bar. The Party starts at 7 PM. Prizes for sexiest Hippie Chick and Grooviest Dude -- judging at 8:30 PM. Enjoy live music and dance to tunes that reach back in time from That Hippie Band from 7-midnight, plus cold drinks and great galley fare. Winners will receive cash prizes and gift certificates. 202 William St.; 305-292-9520; Starts at 7 PM; judging at 8:30 PM. No cover charge or entry fee.

9TH ANNUAL LUV2GLOW PARTY
Do you love to GLOW in the dark? Do you love to dance? LUV2GLOW 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 all night!. Featuring DJ's Jevne, Top Jimmy and special guests. Electronic house music all night, all styles, bumping beats to move your feet! Paint yourself up, wear your best glowing costume, you are all the glowing stars of the party! NO GLOW NO ENTRY $20 cover at the door. 8PM-4AM 21+ -Body painter at the door (additional fee) for those who forgot there glow.

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

DUNGEON of DARK SECRETS
See the Little Black Book at the top of the page for full event details. Tickets will also be available the day of the event at the door. VIP Tickets are guaranteed to sell out so please order them soon. 801 Bourbon Bar - 801 Duval St.

THURSDAY, OCTOBER 28, 2021

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!

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.

Harriette 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. No door charge. Sloppy Joe's 201 Duval Street.Live Stage CamLive Bar CamLive Crowd Cam

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. 9pm-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

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; $

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; $$.

FRIDAY, OCTOBER 29, 2021

BOWTIES & BIRTHDAY SUITS!
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, 1st cocktail, 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 tix at keystix.com

Harriette 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 rlevering@oceankey.com.

GLITTER AND GLOW PARTY
Glitter! Yep, Glitter. And if that’s not enough, a bit of black light to make everything sparkle AND glow! No glitter or glow, no entry! (Well, we’ll probably let you in but seriously, make an effort)! Join us at Sidebar Key West at 504 Angela St (Corner of Duval and Angela). 305-294-0555. Our amazing DJs get things going at 8 PM and the party goes until 4 AM. Drink specials start early and go all night. Prizes for the best glitter/glow get ups.

MASCuerade Affair
See the Little Black Book at the top of the page for full event details. Tickets will be on sale at keystix.com.

KINKY COUPLES PARTY
See the Little Black Book at the top of the page for full event details. Ticket information coming soon. 10:30 PM - 4 AM; 801 Bourbon Bar - 801 Duval St.

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 whenever at Bourbon St. Pub! Clothing Optional. 724 Duval St 305-294-9354

KINKY COUPLES PARTY

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.

© Copyright Fantasy Fest. All Rights Reserved. Digital market
Related Items: 
Festivals