2021 Schedule of Events


2021 Little Black Book Schedule »

2021 Daily Diversions

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

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

REDDY ICE FANTASY FAÇADE COMPETITION
Festively decorated homes and businesses compete for cold hard cash! Free to enter, call 305-295-9112.

SOUND CHECK AT THE GREEN PARROT
Wanna listen to great live music AND still hit the late night party scene? Then come to “Sound Check” at the Green Parrot...the grooviest corner in Key West! Rock your cocktails at this 90 minute preview of our late night gig before you venture out into the playland that is Fantasy Fest...5:30 PM-7 PM 601 Whitehead St. 305-294-6133

Back to the top

Friday, October 22, 2021

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.

HAVANA CABANA POOL PARTY!
Throw on your bathing suit and jump into the largest pool in Key West at the Havana Cabana at Key West! Celebrate with us as we host our very first Fantasy Fest party with local favorite DJ Top Jimmy! Dj Top Jimmy will be serving up the hot beats from 1-5 PM, while our Floridita food truck serves up authentic Cuban food specials. There will be refreshing drink specials available pool side at our Mojito’s pool bar, and games such as giant Jenga, ping pong and cornhole! FREE ADMISSION Noon-5 PM Havana Cabana at Key West: 3420 N Roosevelt Blvd, Key West, FL, 33040. 305-294-5541

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 Amphitheatre! For more info call 305-295-9112. This is a benefit for AH of Monroe, Inc.

Back to the top

Saturday, October 23, 2021

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.

Back to the top

Sunday, October 24, 2021

ZOMBIE BIKE RIDE- A FAMILY FRIENDLY EVENT- NO NUDITY PERMITTED
Rise from the dead and join your newly awakened zombies as they gather at Zombieland in Fort East Martello at 2 PM to get their blood flowing, bodies painted, and mid-afternoon snack from 2-6 PM. Hop on your bike and join the thousands of costumed zombies at 6 PM when the zombie invasion heads down US1 to Duval Street for the Zombiefest in Downtown Key West. Register information coming soon.

ZOMBIEFEST OFFICIAL AFTER PARTIES
Join us after the Zombie Bike Ride and keep the party going with music & dancing in the streets all night long at the following Official After Parties- Tiki House - Bagatelle - Sloppy Joe's - Irish Kevin's - Mangoes - Green Parrot.

Back to the top

Monday, October 25, 2021

THE PERRY HOTEL'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 7001 Shrimp Road, 305-296-1717.

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 25th. 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! For registration and information coming soon. 6PM; Southernmost Beach Resort parking lot, behind the La Mer House at 506 South street.

SOUTHERNMOST FANTASY FEST LUAU
REFUEL with us at the Southernmost Luau after you conquer the SUPER, EVIL, AWESOME Heroes and Villains Run/Walk 5K. Enjoy a Key West style pig roast with your toes in the sand and a drink in your hand. Southernmost Beach Resort, 1405 Duval St. 305-295-6550. 6:30 PM; $45 includes one drink per person. Buffet includes Roast Cuban Pork, Picadillo, Frijoles Negros, Soffritto Rice, Yucca Fries, and Dessert.

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
Are you a Superhero with superhuman powers to protect the universe (or at least Key West)? Or are you the ultimate Supervillain? Come dress as your favorite “Caped” Superhero or Supervillain and party all night. Sloppy Joe’s gift cards will be awarded to best costumes after 9:30 PM. First Place $300 Sloppy Joe’s Gift Card, Second Place $200 Sloppy Joe’s Gift Card and Third Place $100 Sloppy Joe’s Gift Card. Whiskey Kiss on stage at 10:00 PM. 201 Duval Street. Party starts at 8 PM. No door charge.

Back to the top

Tuesday, October 26, 2021

BEACH BASH
Beach Bash: Blast from the Past on South Beach located at the Southernmost Beach Cafe, 1405 Duval Street. 305-295-6550. Join Patrick and the Swazyees in taking you back to the time of surfing, sun-bathing and beach blanket bingo. Put on your favorite beach attire, sport your boldest bikini or don your newest tie-dye. Grab your flip flops and head out to the beach to twist again, like you may have done last summer. Drink and food specials all afternoon along with beach activities and, of course, good old fashion fun! 2 PM- 5 PM.

COCKTAILS FOR ANIMAL TAILS!
COCKTAILS FOR ANIMAL TAILS! LOCATION: Rick's Complex, 202 Duval St. 305-294-4857 TIME: 7-10 PM Admission $35 Come to an “All You Can Drink” Animal Party to benefit the Florida Keys SPCA. Each bar has been transformed into a different Animal Kingdom around the world where you can enjoy an All You Can 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 great prizes! Proceeds will benefit the animals of the Florida Keys SPCA. Pre-sale tickets are available at at 5711 College Rd. 305-294-4857.

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.

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.

MEN OF LABARE TIGHTY WHITEY PARTY
Men of LaBare as seen in the movie "Magic Mike". It's the sexiest and wildest all male review show on Earth. Join the world famous LaBare dancers for an ultimate night of complete satisfaction. Sexy white wear is encouraged for this party and couples are welcomed. Bottle Cap 1128 Simonton St., 9pm to 4am. Limited tickets are available for this event and can be purchased at keystix.com or call 305-304-1188. $

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! 601 Whitehead Street 305-294-6133

Back to the top

Wednesday, October 27, 2021

WASTING AWAY @ THE ORIGINAL MARGARITAVILLE
Dress like a Tourist and Come Get Lei'd @ The Original Margaritaville! We will be offering a different specialty concoction every hour beginning at 11AM until close. Along with each specialty drink comes a different colored lei. So cruise back in throughout the day, buy another drink and get another lei on us! How many different colored leis can you get? 500 Duval Street 305-292-1435

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

ROCK AND ROLL REVITALIZING 1960’S POOL PARTY PRESENTED BY BLUE CHAIR BAY RUM
Let us take you back to a groovy time full of Tom Collins, Pink Squirrels and Greyhounds; when the bikini became every woman’s new purchase, mini-skirts crept into closets and good ol’ Rock and Roll was heard from every radio station and record player in the United States. Dress in your favorite vintage swimsuit, psychedelic patterns and platform shoes and join us at the Marker Waterfront Resort for The Sixties Pool Party. Boogie down to live music your old man might not approve of, sip on a few of our nifty drink specials and have a guaranteed far out time. Do you dig? Featuring Patrick and the Swayzees Live Poolside! The Marker Waterfront Resort, 200 William Street. 305-501-5193. 1-4 PM. Live Webcam

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 your 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 2PM at The Conch Republic Seafood Company, 631 Greene St. Ticket info coming soon.

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].

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. Emceed by Magic Frank Everhart. 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. Join us after the Bud Light Fantasy Fest Parade for a walk on costume contest!! Strut your stuff and win groovy prizes!! Live Webcam

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

ABC PARTY
Hooters Super Model Jessie Teschker and Celebrity Girlfriends are your Host for This Adventurous and Risque Party of a Lifetime. Enter the ABC (Anything But Clothes) Costume/Body Painting contest and win $700 in cash and prizes. It's the most outrageous and creative contest on the planet! Featuring Various Wow 92.7 DJS Limited VIP tickets are available to the public for this private, star-studded red carpet celebrity extravaganza. Purchase tickets at keystix.com or call 305-304-1188. Sandbar Sports Grill 511 Greene St, 10 PM.

DUNGEON of DARK SECRETS
See the Little Black Book at the top of the page for full event details. Click here to purchase your advance tickets. 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.

Back to the top

Thursday, October 28, 2021

BERKSHIRE HATHAWAY PARADE OF HOMES MEGA OPEN HOUSE EVENT
Berkshire Hathaway Knight & Gardner Realty invites you to their Parade of Homes Mega Open House Event! Sign up at any of their open houses for a chance to win 4 tickets to their annual Parade Party at their office at 336 Duval Street. More info coming soon.

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 wants 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!

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 danteskeywest.com for more details.

39th ANNUAL HEADDRESS BALL
The Key West Business Guild presents the 39th annual Headdress Ball on Thursday, October 28, 2021 at 8 pm. This is the premier LGBTQ+ event of the Fantasy Fest celebration and the event proudly returns to the new Key West Amphitheater at the Truman Waterfront Park. Tom Luna returns as the outrageous EmCee with Rude Girl from WEOW 92.7 radio rocking out our sound. Randy Roberts will open the show and is joined by some of the best of Key West local talent, including Christopher Peterson and the cast of the Waterfront Playhouse’s Rocky Horror Picture Show! Over twenty contestants will parade their Headdress creations on the amphitheater stage to vie for the $3,000 first prize.

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. Live Webcam Live Party Cam

SLOPPY JOE'S 42nd ANNUAL TOGA PARTY
Toga! Toga! Toga! 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!” Transport yourself back in time with a traditional ancient Toga or dare to create your Toga using Fantasy Fest theme “All A Daze for a Holiday ” Best Togas will win Sloppy Joe’s gift cards throughout the night. Groups of 2 to 8 people may participate in our Toga Ceremony to award best Togas at 9:30PM. To enter Toga Ceremony groups must sign up next to the stage between 8:00 PM-9:15 PM. Audience will choose winner. First Place $300 Sloppy Joe’s Gift Card, Second Place $200 Sloppy Joe’s Gift Card and Third Place $100 Sloppy Joe’s Gift Card. Contestants must be dressed in a toga. Body paint is not a toga, but may be used as part of the toga costume. Free to participate. Limited Toga sheets are available for purchase in the Sloppy Joe’s Retail Store for $10 (Proceeds to AH of Monroe County ). Cherry on Top Band from Cincinnati, OH on stage after Toga Ceremony. Sloppy Joe's 201 Duval Street. Door charge. Live Stage Cam Live Bar Cam Live 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
“Save the Ta-Tas!” A portion of the proceeds will be donated to the American Cancer Society - Making Strides Against Breast Cancer of the Florida Keys. Wear your sexiest pink costume or body painting to the best party on Thursday night. Costume contest with a $500 bar tab for 1st place, $250 bar tab for 2nd place and $100 bar tab for 3rd place. Live entertainment by DJ Buggy. Party favors while supplies last. 305 Duval St.305-296-9373; 9 PM; $

PAJAMA AND LINGERIE PARTY
So Many Playmates, Bunnies, and Models pay tribute to Mr. Playboy himself, La Hef at this Legendary Party. This Event is surreal and makes you feel like you are at the mansion. Enter the $700 Hugh Hefner and Marilyn Monroe look-a-like contest. Mingle with celebrities plus enjoy guest DJs live. Dress in Sexy Nightwear. Purchase Advance VIP tickets online now before they sell out at keystix.com or call 305-304-1188. .;10 PM.$

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; $$.

Back to the top

Friday, October 29, 2021

NOCHE LIBRE
Grab your fedora and cigar and get ready to experience Cuba’s glory days at the Havana Cabana at Key West! Come ready to dance and win prizes at our Salsa Dance Off, to the music of our very own Floridita Salsa band performing 1-5 PM! Enjoy Floridita’s live performance with one of over 15 different types of Mojitos from our Mojito’s pool bar. And don’t forget to bring your bathing suit! With the largest pool in Key West, we have plenty of room for everyone to escape the Key West heat! With great food specials, free give ways, specialty cocktails, games like giant Jenga, ping pong and corn hole, Noche Libre will be a great time for all ages! FREE ADMISSION NOON -5 PM Havana Cabana at Key West: 3420 N Roosevelt Blvd, Key West, FL, 33040. 305-294-5541

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 noon-5 PM. Buy tix at keystix.com

DAY AT SOUTHERMOST 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

FANTASY FEST STREET FAIR
Duval Street's mile-long eater-tainment extravaganza features arts and crafts, food vendors, lively libations and costumed frivolity; Noon to 10 PM. Live Sloppy Joe's Street Cam Live Rick's Street Cam

SAN CARLOS STREET PARTY
Latin Music! Mojitos! Rum! Dancing! General Merriment! Noon - Midnight! 516 Duval St 305-294-3887

BOURBON ST. PUB'S TEA IN THE STREET AND POOL PARTY
The BIGGEST dance party in the street during Fantasy Fest 2021,. Get your groove on while dancing and drinking on Duval St. Live DJs, Boys, Beads and Booze, Drag Queens, celebrities and MORE! 12 PM until whenever. FREE Dance party ; as well as "Splash" Pool Party in the New Orleans House Garden & Pool Bar. Event is Open All! Noon-5pm Join the party at 724 Duval St. 305-293-9800 Bourbonstpub.com

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

MASQUERADE MARCH
Join the crowd as they parade through Old Town with music and noisemakers! Thirst quenchers provided at selected guesthouses. Begins at the Key West Cemetery Frances Street entrance but revelers can join the mad march anywhere along ONE routes! Start marching at 5:30 PM; All welcome; FREE.

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 [email protected].

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.

PIMPIN AINT EASY
This event is guaranteed to satisfy all your erotic dreams. Join the King Pimp himself Ron Jeremy, and so many Sexy Adult Movie Stars for the wildest party of your life! Enter the $700 Mr. Pimp and Ms. Ho costume contest. Plus dance to the music of celebrity DJs mixing live on stage. This event sells out every year. Purchase Advance VIP Tickets online at keystix.com ; or call 305-304-1188

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.

Back to the top

Saturday, October 30, 2021

DUVAL STREET PROMENADE
Sassy entertainers, enticing food and spirited libations tempt costumed merrymakers as they party from the Gulf to the Atlantic; Noon to 10:30 PM; FREE. Live Sloppy Joe's Street Cam Live Rick's Street Cam

BOURBON ST. PUB'S VIP PARADE 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 "All A Daze for the Holidays" 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 Nicole 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.

DIRTY DOCTORS AND NAUGHTY NURSES PARTY
It's the most pleasurable trip you have ever had to the hospital. As seen on TV, join Hot Marilyn Monroe Look alike Model Michelle Victoria Adams and her VIP Celebrities girlfriends for the official parade after party plus dance to world renowned DJs all night. Enter the $700 Dirty Doctors and Naughty Nurses costume contest. VIP Tickets are in high demand! Purchase them now before they sell out at keystix.com. or call 305-304-1188; Key West Theater 512 Eaton St; 10 PM

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.

Back to the top

Sunday, October 31, 2021

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.

THE AFTER PARTY AT THE MARKER
You've made it to the last day of Fantasy Fest!!! You deserve some R&R. Spend the last day of Fantasy Fest recovering by the pool with Hangover Hospital. The best way to cure a hangover. The Marker Waterfront Resort, 200 Williams St. Noon-4 PM Free

“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.

Back to the top