So, Hope you all enjoyed the Goombay Street Festival this weekend! This event kicks off the start of Fantasy Fest here in Key West. The street fair is a lot of fun, with vendors peddling all types of wares and wonderful Bahamian foods being sold to event goers. This is one of the more tame events when it comes to Fantasy Fest. So everybody prepare for some crazy parties this week!
Some of the more well known parties include Captain Tony’s Plaid Party, the Head Dress Ball, the Pet Masquerade (my personal favorite), Sloppy Joe’s Toga Party, and the Pimp and Ho Party. Of course there are many, many more events during this time. You can actually check them out here!
Have fun and be safe as you enjoy Fantasy Fest this week. And if you didn’t make it down this year, start planning now for next year, as many hotels sell out almost a year in advance!
2026 Fantasy Fest Schedule of Events
FRIDAY, OCTOBER 16, 2026
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 Emma Street and features nonstop musical entertainment ranging from reggae to soca. This is a family-friendly event. Noon to midnight; FREE.
BARBIE’S PINK POOL PARTY FOR BREAST CANCER AWARENESS AT THE MARKER
Wear your Best Barbie or Ken pink costumes and join The Marker Key West Harbor Resort with DJ El Grace for a fun pool party that will also make you feel good! Along with great music, we’ll have a Barbie or Ken costume contest, Barbie pink pools, Barbie pink drink specials, pink food specials, and more – all to benefit Womankind Key West… $20 donation – 4-7PM.
ROYAL CORONATION
Join the Florida Keys SPCA at the 2025 Neonimal Royal Coronation where we will celebrate all 4 candidates at the culmination of their 6 week fundraising campaign. Kick off Fantasy Fest to see who becomes the King & Queen of Fantasy Fest 2025! This fabulous 2-hour stage show includes entertainment by local celebrities and the candidates themselves! Tickets include reserved seating, a 3-course plated dinner by Catered Affairs and two votes for the candidates of your choice.Get your tickets today! General Admission Entry is FREE with open lawn space for self-seating. Cash bar for all. This evening is hosted at Key West’s Coffee Butler Amphitheater. 6PM Doors, 7PM Show. For more info, contact [email protected].
Hush Money
This fresh, fabulous new drag show is hosted by winner of Best in Drag at the 2026 Bubba Awards in Key West, Beatrix Dixie. HUSH MONEY dives headfirst into a deliciously naughty world of fame, fortune and temptation. Expect brand-new material, iconic drag classics, killer looks, comedy, glamour, and unforgettable performances from some of the best drag talent Key West has to offer. One minute you’ll be laughing, the next you’ll be gagging—and you may leave knowing a few things you probably weren’t supposed to hear.
SATURDAY, OCTOBER 17, 2026
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 Emma Street and features nonstop musical entertainment ranging from reggae to soca. This is a family-friendly event. Noon to midnight; FREE.
RUM WITH BUM
Key West’s Fire Chief Joseph “Bum” Farto went missing in 1976 under mysterious circumstances. Rumor has it he can be found at the Alex Vega Key West Firehouse Museum! Snap your photo with El Jefe to prove you found him and the museum will reward you with a tasty shot of Pyro Punch. Free Admission and rum shots. Donations appreciated. Join us 10-2pm at Alex Vega Key West Firehouse Museum – 1024 Grinnell Street.
LIP SYNC & LIFE GUARD POOL PARTY at the BLUE FLAMINGO RESORT
Grab your swimsuit, channel your inner superstar, and dive into the most over-the-top pool party of Fantasy Fest! The Lip Sync & Lifeguards Pool Party is turning The Backyard Pool & Social Club at Blue Flamingo Resort into a sun-soaked stage where beachside glamour, Broadway drama, and Fantasy Fest energy collide. Whether you’re serving lifeguard realness, bringing your best diva-inspired poolside look, or simply soaking up the spectacle, this is your chance to let your personality shine. Expect a lively afternoon filled with iconic singalong anthems, poolside performances, spontaneous lip sync moments, outrageous costumes, and plenty of unforgettable Fantasy Fest fun. Strike a pose and capture the moment at our themed photobooth, gather your friends for poolside selfies, and show off your Fantasy Fest style while enjoying the vibrant atmosphere that only Key West can deliver. Sip, splash, and celebrate with food and drink specials available throughout the event, featuring refreshing cocktails, frozen favorites, and delicious bites perfect for a day in the Florida sun. Lounge poolside, cool off with a swim, or take center stage because at this party, the pool is your spotlight. Best of all, there’s NO COVER CHARGE and FREE PARKING, making it the perfect stop on your Fantasy Fest itinerary Blue Flamingo Resort – 3820 N Roosevelt Blvd – 12-4PM.
THAT ARENA ROCK SHOW AT SUNSET PIER
FREE Concert at the Sunset Pier! Get ready for the ultimate high-energy, theatrical tribute to Classic Rock & Roll! That Arena Rock Show is performing legendary rock anthems that ruled the airwaves in the ’70s and ’80s. This show will take you on a trip back in time, turning Sunset Pier into a full-blown rock arena for the night! Get your lighters out and your fists in the air—this is more than just music, it’s an absolute experience. Grab your friends, grab a drink, and get ready to rock against the backdrop of Key West’s best sunset! Begins at 7PM. Ocean Key Sunset Pier – 0 Duval Street. Ocean Key Sunset Pier’s Live Cam
PARTY IN MY PANTS: A SEXY CABARET
This Fantasy Fest, the hottest party, isn’t on Duval Street. It’s in my pants and everybody’s coming! Join music icon, Johnny Showcase (America’s Got Talent Season 18), for a gloriously unhinged collision of outrageous comedy, jaw-dropping circus, and spectacular burlesque. Set to the greatest party and make-out soundtrack ever created, P.I.M.P. takes over the Key West Theater October 17 & 19 to 23 with a no-holds-barred spectacle of world-class performers, iconic songs, unforgettable moments, and enough sexy, ridiculous fun to keep the party going all night long! Tickets available at KEY WEST THEATER Doors 7:30 PM | Show 8:00 PM.
SUNDAY, OCTOBER 18, 2026
KEY WEST ARTISAN MARKET at HIGGS BEACH
Don’t miss the Key West Artisan Market at Higgs Beach, Fantasy Fest edition, Sunday, October 18 from 10 am to 2 pm! Shop fine crafts and art from talented Florida Keys makers, grab your official Fantasy Fest merch, and enjoy delicious international food trucks and stalls—plus refreshing adult beverages and live music!
ZOMBIE BIKE RIDE- A FAMILY FRIENDLY EVENT
Mark your calendars and get Zombie on your brains! The Rock & Roll costumed Halloween bike ride that attracted over 7500 bicycle enthusiasts at a time -is back! Zombie returns for another wild run from East Martello to The Coffee Butler Amphitheater. Join your newly awakened zombies as they gather at Zombieland in Fort East Martello at 2 PM for the newly expanded Kids Zone with bounce houses and more! Body painting, food vendors and full bar is on the grounds of the starting area 2-6 PM. Hop on your bike and join the thousands of costumed zombies at 6 PM when the zombie invasion heads down A1A to downtown Key West for the FREE Zombiefest Dance Party at the Coffee Butler Amphitheater presented by RamsHead.
ZOMBIELAND
Before the Ride! Join in the fun early as we gather at Zombieland in Fort East Martello starting at 2 PM for the newly-expanded Kids Zone with bounce houses and more! Body painting, food vendors and a full bar is on the grounds of the starting area 2-6 PM.
ZOMBIE PARADE WATCH PARTY
Join us from 5 to 7 PM, don’t miss the Zombie Parade Watch Party! Bring your lawn chair and camera to catch thousands of the undead bike by in all their ghoulish glory. Food and a full bar will be available to fuel your festivities! It’s all happening Sunday, October 19th, at the corner of White Street and Atlantic at the Key West Artisan Market. See you there!
ZOMBIE BIKE RIDE OFFICIAL AFTER PARTY
Celebrate completing the wildest ride of the year with a DJ After Party at the Coffee Butler Amphitheater. FREE entry to the Official End of the Ride Event with Food Vendors, Full Bar, AND three huge bands — Electric Kif, Sueñalo and Afrobeta — rocking the Zombie Stage! If the ride’s not for you, you can still be a part of the action and watch the Zombie Mob roll in. Amphitheater opens at 6PM.
LEDGENDS NEVER DIE: Día de los Muertos Celebration of Musical Icons
The legends are back—and they’re ready for an encore! Celebrate Día de los Muertos with an unforgettable afternoon and evening honoring the music of legendary icons whose voices, style, and songs continue to live on. Join us at Elevate Skye Bar & Lounge at Opal Key Resort & Marina from 3PM – 7PM for Mexican and Latin-inspired drinks, art, food, dancing, and festivities. Come dressed in traditional Día de los Muertos attire and celebrate the vibrant colors, beauty, and spirit of this beloved tradition, with music inspired by the legendary sounds of Selena, Prince, David Bowie, Amy Winehouse, Celia Cruz, Jerry Garcia, Jimmy Buffett, Dolly Parton, and beyond. Want to channel your inner Lolita? Enter the Lolita’s Look-a-Like Contest HERE for your chance to compete for a cash prize! $5,000 first-place prize, followed by a $2,500 second-place prize and $1,000 third-place prize. At 6:45PM gather for a special sunset tribute and toast to the legends who continue to inspire us. $30 Pre-sale tickets available HERE. Day of Ticket costs to increase. Come dressed in your Día de los Muertos best, ready to celebrate, dance, and honor the musical legends whose music will never die! Event Policies: This is a 21+ event, and guests must wear their event-issued wristband for the entire event. The guest’s name must be provided on each ticket purchased. Tickets are non-transferable and non-refundable. No outside food or beverages, pets, smoking, or vaping are permitted. Elevate Skye Bar & Lounge | 245 Front Street | 3-7PM (Doors @ 3PM)
FREEDOM ROCKS ICONS: SEXY 60’s & 70’s PARTY
The Green House | 431 Front St., Key West | 5–7 PM. Fantasy Fest is going retro! Step back into the decades when the music was loud, the fashion was wild, and the rules were optional. Break out the bell bottoms, fringe, go-go boots, leather, sequins and psychedelic prints and channel your favorite 60’s or 70’s rock icon. Come ready for iconic music, cold drinks, groovy vibes and plenty of Key West fun. Dress like a rock legend, disco queen, go-go dancer, flower child—or just show up ready to party. Get loud. Get groovy. TURN IT UP! Peace. Love. Rock ’n’ Roll. And a little Key West trouble.
AFTERLIFE: THE AWAKENING
Step into the forbidden garden of desire at Bourbon Street Pub. This one-night experience transforms the Garden into a realm of aerial burlesque performed over the pool, voyeur shower stations, and sensual performances that ignite every sense. Guests will wander through seductive zones designed to tempt and tease, leading up to electrifying stage shows and free-flowing encounters that set the tone for the week ahead. This isn’t just a party — it’s the erotic heartbeat of Fantasy Fest. Bourbon Street Pub – side entrance, $125 single $175 couples, Doors will open 7 PM, Tickets available at the New Orleans House starting September 1st; 8 AM-7 PM. 305-293-9800 | 724 Duval Street | Or at Keystix.com – TICKETS
THAT ARENA ROCK SHOW AT SUNSET PIER
FREE Concert at the Sunset Pier! Get ready for the ultimate high-energy, theatrical tribute to Classic Rock & Roll! That Arena Rock Show is performing legendary rock anthems that ruled the airwaves in the ’70s and ’80s. This show will take you on a trip back in time, turning Sunset Pier into a full-blown rock arena for the night! Get your lighters out and your fists in the air—this is more than just music, it’s an absolute experience. Grab your friends, grab a drink, and get ready to rock against the backdrop of Key West’s best sunset! Begins at 7PM. Ocean Key Sunset Pier – 0 Duval Street. Ocean Key Sunset Pier’s Live Cam
MONDAY, OCTOBER 19, 2026
HAVANA CABANA AT KEY WEST’S DUCK, DUCK, BOOZE POOL PARTY
Don’t miss the duckie takeover at Havana Cabana at Key West! 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, and swag. Duck floats, duckie bathing suits, duckie tutus, and creativity are encouraged! This event is FREE and open to the public, (adults only)12pm-4pm. Havana Cabana at Key West, 3420 N. Roosevelt Blvd., 305-294-5541.
MARILYN MONROE MONDAY MARATHON
All Day. One Icon. Countless Classics. Join us for a full day dedicated to Hollywood’s most unforgettable blonde bombshell. Diamonds, red lipstick, and that unmistakable wink. Grab a seat any time between 10AM and 10PM and stay as long as you like. Popcorn’s popping, doors are open. 7PM — Costume Contest Channel your inner icon and dress the part for a chance to win prizes. Best look takes the crown. Tropic Cinema- 416 Easton Street.
MRS. ROPER ROMP
Get your Caftans ready and that signature curly red wig for a groovy party filled with stunning sunsets, music, photo opportunities, dancing, trivia, games, prizes and funtastic specialty drinks! Come and Knock On Our Door for all the Three’s Company Fun you can stand! This is not a ticketed event but we do ask that you bring your rent money because 100% of rent will go directly to a local charity!Presented by Sunset Pier & Femme Fatale Body Art Call 850-596-4065 for info. 5PM – FREE 0 Duval Street
A GREEN PARROT BEATLES TRIBUTE
All You Need is Love… and Popcorn. Join Key West’s very own BEATLE BAND at The Green Parrot with shows at 5:30 and 9:00 and 11:00pm. Their past Beatle Tribute shows had Parrot patrons swinging from the rafters as they danced, laughed, and sang-along to a setlist pulled from decades of Lennon-McCartney hits. 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! Green Parrot Bar – 601 Whitehead Street – 5:30pm, 9:00pm, 11:00pm – Free Shows
FANTASY FEST 5K RUN/WALK
Ready to Rock Fantasy Fest? We are excited to be the Official Monday Night Party! Come RUN/WALK with us and see why it’s More Than a 5K… It’s a PARTY! Whether you run, walk, dance, or sing your way to the finish, this race is all about having fun! Follow the course through the heart of Key West, enjoy live music vibes, and make a stop at the famous Shot Station for a complimentary shot along the way. As always, Reef Relief is our Charity Partner! Cross the finish line to earn your blingy finisher medal, then keep the party going at the Post-Race Party at Tiki House Key West. Click HERE to Register.
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.
MASQUERADE MONDAY WINE DINNER PRESENTED by BOGLE WINES
Step into an evening of mystery and elegance at our High-Society, Great Gatsby Roaring Twenties Era. Masquerade Ball + Wine Tasting Dinner featuring Bogle Wines. Dress the part in your favorite mask and costumes and enjoy a night where fine wine, exquisite food and live music and entertainment comes together. Savor a multi-course dinner paired with wine, while the music sets the mood for a magical night of intrigue and celebration. $185 includes dinner, wine, and gratuity. Cocktails will be charged on consumption. A&B Lobster House – 700 Front St | Doors @ 6PM | Welcome drink @ 6:30PM | Dinner @ 7PM Masks are REQUIRED, seats are limited
KINKY CARNIVAL
Key West’s Original Fantasy Fest Kink Party in its 28th year! Ticket includes: 3 hour Open Bar from 8pm – 11pm, but the party goes until 1am! Interactive BDSM stations, Fetish rooms, Bondage and more! You can snag tickets from Friday, October 18th, through Sunday, October 19th, between 1 pm and 9 pm. We’re also selling tickets on Monday, the 20th, starting at 1 p.m. and going strong all night. $75 | Cash Only No Kinky Costume | No Entry First Flight – 301 Whitehead Street.
“WICKED” SING-ALONG MOVIE NIGHT IN THE COURTYARD
Adam & Eve | 524 Front Street. Join us for a free showing of Wicked under the stars in our shared courtyard. Dress to impress — prizes await the best Wicked-related costumes, and Adam & Eve will have themed costumes and pieces available for purchase to complete your look. The Southernmost Pint will be serving up their amazing craft beers, wine, food and more, for purchase throughout the night. Sing, dance and enjoy the show! Starts at 7:30pm
PARTY IN MY PANTS: A SEXY CABARET
This Fantasy Fest, the hottest party, isn’t on Duval Street. It’s in my pants and everybody’s coming! Join music icon, Johnny Showcase (America’s Got Talent Season 18), for a gloriously unhinged collision of outrageous comedy, jaw-dropping circus, and spectacular burlesque. Set to the greatest party and make-out soundtrack ever created, P.I.M.P. takes over the Key West Theater October 17 & 19 to 23 with a no-holds-barred spectacle of world-class performers, iconic songs, unforgettable moments, and enough sexy, ridiculous fun to keep the party going all night long! Tickets available at KEY WEST THEATER Doors 7:30 PM | Show 8:00 PM For more information go to PartyInMyPants.show Warning: Side effects may include spontaneous parties in your pants too.
SLOPPY JOE’S COMIC BOOK CAPE-ERS PARTY
Come dressed as your favorite “Caped” Superhero or Supervillain and party all day and night. Live music on stage all day! Dancing starts at 5:30pm, Turning The Tide on stage following contest, plus our house DJ will keep you dancing all night. To enter costume contest sign up next to stage at 8:15pm, contest on stage at 9:00pm. You may enter contest as an individual or as a group of 2-4 people (must be in costume). Prizes: 1st place $500 Sloppy Joe’s Gift Card; 2nd place $250 Sloppy Joe’s Gift Card; and third place $100 Sloppy Joe’s Gift Card. Other giveaways throughout the night. Sloppy Joe’s 201 Duval Street.
TOPS OR BOTTOMS UNDERWEAR PARTY
Underwear party 10pm-4am. Private Underwear party – men’s event. You must lose one or the other.! Free clothes check. In the New Orleans House Garden & Pool Bar; 305-293-9800; 724 Duval St.
TUESDAY, OCTOBER 20, 2026
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. $10 Cover Dante’s Restaurant and Raw Bar, 951 Caroline St., 305-293-5123.
FLORIDA KEYS COUNCIL OF THE ARTS FANTASY FEST POSTER SIGNING PARTY
Come meet the winning 2025 Fantasy Fest poster designer, get your Official Fantasy Fest poster signed and pick up other 2025 Fantasy Fest T-Shirts and Swag! Swing by La Concha Hotel from 3 – 5pm. 430 Duval Street.
GREATEST HITS POOL PARTY at WINSLOW’S BUNGALOWS
Dress Like an Icon. Sing Like a Legend. Dress as your favorite headliner. Grab the mic and own the stage with all-day poolside karaoke. Dance between sets as the DJ keeps the party going. Stock up on glitter, tutus, and Fantasy Fest favorites at our Merch booth. Prizes for Best Dressed and Best Performance. Hotel Guests Only: VIP Backstage Pass with reserved seating at the pool party, complimentary cocktails, and an exclusive welcome swag bag. Located at 725 Truman Avenue from 12 PM to 4 PM.
CASA CABARET
Step into the spotlight at Casa Cabaret, a Fantasy Fest celebration at Casa Marina Key West where historic glamour meets island fantasy. Join us for an evening of live entertainment, cocktails, bites and cabaret-inspired revelry in one of Key West’s most iconic oceanfront settings. Come ready to sip, socialize and kick off the Fantasy Fest festivities with a little extra glamour. 4–7PM. | Casa Marina Key West | 1500 Reynolds Street
WE LOVE DOLLY! – A DOLLY PARTON TRIBUTE PARTY
The Green House | 431 Front St., Key West| 4–7 PM Grab your rhinestones, tease that hair to the heavens and get ready for a Fantasy Fest celebration of the one and only Dolly Parton! We’re bringing the big hair, country glam, Dolly hits, cold drinks and plenty of sparkle to The Greeen House. And don’t forget the Dolly Costume Contest! Come dressed in your best Dolly-inspired look and go all out—big hair, fringe, sequins, cowboy boots and over-the-top Dolly style are highly encouraged. Come ready to sing, strut and celebrate an icon. The higher the hair, the closer to Dolly.
COCKTAILS FOR ANIMAL TAILS! PRESENTED BY DIRTY MONKEY.
Rick’s Complex – 202 Duval St | 8 – 11PM (7:30 PM if you Pre-Purchase Your Ticket!) Party for a purpose at our official Fantasy Fest charity event to benefit the homeless animals of the Florida Keys SPCA. Your $40 entry fee will include Unlimited Drinks throughout the entire Rick’s Complex. Dress in your most wild costume for the FREE costume contest with a $500 grand prize! Get ready to party like an animal! TICKETS Questions? Email: [email protected]
TAY TAY TUESDAY
Calling all Swifties, You know what to do! Sunset Pier is bringing you A LIVE Taylor Swift Tribute concert performed by local star Meghan Barter. 6PM – 9PM FREE 0 Duval Street.
TUTU SALSA SESSIONS
In honor of Tutu Tuesday, join us at the Southernmost Beach Café for $22 bottomless mimosas (2hr max) throughout the day. Then join us for a fun evening of Salsa dancing while wearing your tutus, lessons by Salsa John, sponsored by Dulce Vida Organic Tequila and Bogle Family Vineyards. Enjoy margarita and sangria specials while you dance your tutus off – 7pm, Southernmost Beach Resort – FREE!
PARTY IN MY PANTS: A SEXY CABARET
This Fantasy Fest, the hottest party, isn’t on Duval Street. It’s in my pants and everybody’s coming! Join music icon, Johnny Showcase (America’s Got Talent Season 18), for a gloriously unhinged collision of outrageous comedy, jaw-dropping circus, and spectacular burlesque. Set to the greatest party and make-out soundtrack ever created, P.I.M.P. takes over the Key West Theater October 17 & 19 to 23 with a no-holds-barred spectacle of world-class performers, iconic songs, unforgettable moments, and enough sexy, ridiculous fun to keep the party going all night long! Tickets available at KEY WEST THEATER Doors 7:30 PM | Show 8:00 PM For more information go toPartyInMyPants.show Warning: Side effects may include spontaneous parties in your pants too.
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.
TUTU TUESDAY PRE-PARTY BAR CRAWL
Gather your friends, all the nerds, cartoon kids, dweebs, hallway weirdos and full grown tutu-monsters and join the Tutu Tuesday Pre Party Parade! Step off with us at 6:00 PM sharp from Mary Ellen’s for the after-school special no one warned you about! Your parade pass includes entry to the legendary Tutu Party—just be sure to check in early and snag your wristband before we roll out! Get your tickets (new link) and check in with us at Mary Ellen’s 420 Appelrouth Ln starting at 4:30pm. Ticket includes bar stroll and entry to the Tutu Party! VIP packages also available. TICKETS Mary Ellen’s – 420 Applerouth Lane
16th ANNUAL TUTU TUESDAY – NERDELODEON
This year’s theme is NERDELODEON — part after-school special, part cartoon fever dream, part Revenge of the Nerds energy. Jocks, geeks, dweebs, teachers’ pets, hallway weirdos, cartoon kids, and full-grown tutu monsters all end up at the same party — all in tutus, of course. We’re taking over the Caroline Street district with 10+ DJs across 4 bars in Downtown Key West. General Horseplay is home base. Pick up your wristband there, then bounce around 4 bars packed with DJs, lights, lasers, tutus, silliness, other surprises, and nerdy little chaotic worlds. One wristband gets you into the whole goofy mess. As always, forever and ever: No Tutu. No Entry. 6PM-2AM
WEDNESDAY, OCTOBER 21, 2026
SLOPPY JOE’S SLUMBER PARTY
Dreaming of the Best Party in Town? Roll out of bed & head to Sloppy Joe’s Slumber Party with live music starting at 10am! Be creative, be goofy, but be dressed in SLEEPWEAR! Will it be a onesie, flannel jammies, boxers or your favorite lingerie? You decide. Create your outfit around the Fantasy Fest theme “Musical Icons & Iconic Musicals”. Enter our costume contest & win big! 1st Place $500 Sloppy Joe’s Gift Card; 2nd Place $250 Sloppy Joe’s Gift Card; 3rd Place $100 Sloppy Joe’s gift card. Sign up begins at 8:15pm next to the stage with the contest starting at 9:00pm. Enter the contest as an individual or group of 2-4 people (must be in costume). “Nightbreakers” takes the Sloppy’s Stage following the contest to keep you dancing all night long! Sloppy Joe’s 201 Duval Street. #STILLTHEBESTPARTYINTOWN
SWAYZEES 90’s NEON POOL PARTY AT SOMO’S SHORES POOL
Grab your retro 90’s neon swimsuit and come dance, swim and drink with Les Greene and the Swayzees! Beyond his talent as a solo artist, Les Greene is also known for his dynamic live performances. Whether he’s commanding the stage with his soulful voice and blistering guitar solos or leading the tight-knit full band, The Swayzees through a funky groove; Greene is a consummate entertainer, capable of captivating audiences with his boundless energy and magnetic stage presence. His live shows are a testament to the transformative power of music – a shared experience that brings people together and leaves them uplifted and inspired. 2-5pm. FREE!
FANTASY FEST TRIVIA – SOUTHERNMOST BEACH RESORT
Bring all you favorite guys and ghouls for a one-of-a-kind TRIVIA experience. This spooky Fantasy Fest trivia features all the fun decorations of a proper Halloween Party, 6 great rounds of Trivia, Creepy drink specials, and the BEST part of all… all players in costume receive 5 bonus points! Reservations are a must; tables will fill fast! 6pm Sharp! FREE!
THE GOLD PARTY
Come celebrate 50 Years of Fabulous at the Best Gay Men’s Resort in The World! No clothing required, but wear something GOLD! Gold crowns, tiaras, body paint, sequins, spandex- you name it- just make it GOLD! Tons of free appetizers served by Golden pool boys, free shots, giveaways, and 2-4-1 on all cocktails! All gay, bi, queer, trans + brothers welcome. Party goes 5-8pm @ 1129 Fleming St.
ALIEN ABDUCTION PARTY
The Green House | 431 Front St., Key West | 6–8 PM. Aliens always seem to abduct people in the middle of the night, so this Fantasy Fest, we’re showing up prepared—IN OUR PJs. Throw on your pajamas, robe, slippers, sleep mask, alien gear or whatever you’d want to be wearing when a mysterious beam of light suddenly pulls you out of bed. Join us for cold drinks, cosmic vibes, out-of-this-world fun and all the weirdness you’d expect from Fantasy Fest in Key West. Aliens, Earthlings and abductees are all welcome. If you wake up Thursday with no memory of the night before… blame the aliens.
PET MASQUERADE
Join us for our famous Pet Masquerade Event. You will see a carousel of frisky pets and playful owners performing for fame, fortune and prizes beginning at 6:30PM on the stage of the Key West Amphitheater at the Truman Waterfront Park! Think you and your furry, feathered or slithery friend have the purrfect outfit? Four categories to enter including Junior, Pet/Owner Lookalike, Most Exotic, Best Theme Adaptation, as well as Overall Winner/Best in Show-$25 each entry; benefits the Monroe County Sheriff’s Office Animal Farm; 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. Food and beverage available on site. 21 E. Quay Rd.
STUDIO 69 DISCO PARTY
Viva Argentinian Steakhouse | 903 Duval Street | 6PM till Midnight – A throwback to the era that started it all! Whether you have Saturday night fever of a Charlie’s Angels fetish, if there was any reason for a disco ball then this is it. Break out your most fabulously funky costumes and come dance the night away with our local DJs Scott Gerke & Chros Cohen! Tickets : $15 1 Drink / $60 2hs-Open Bar / $95 2hs-Open bar + Special Dinner Menu. Open Bar 6pm till 8pm. First come, First Served
The 5th ANNUAL PARTY LIKE A ROCKSTAR
Kaya Island Eats at the Key West EmPOURium | 618 Duval Street | 6 PM–Midnight. Get ready for one of Fantasy Fest’s most electrifying nights, featuring live music, incredible costumes and pure rock ’n’ roll energy! 8 PM: Guitar Shred-Off featuring outstanding local and out-of-town musicians competing for cash prizes! 9 PM: Jeff Clark’s All-Star Band takes the stage for a powerhouse live performance! 10 PM: Costume & Air Guitar Contest with cash prizes! Dress as your favorite rock star and bring your wildest stage presence. Come dressed to rock. Come ready to party. Don’t miss the 5th Annual Party Like a Rock Star!
33RD ANNUAL HOMEMADE BIKINI CONTEST
Over $2500 in cash prizes. Creativity and attention to detail are the key to winning the first place prize of $1000! Additional cash prizes for 2nd and 3rd place. Plus a People’s Choice Award! Hosted by World-Famous Emcees and Local Celebrities, Mr. Bill Hoebee and Carolyn G. This year you have an opportunity to join our celebrity judges panel. Don’t miss out on the early entry option to secure a seat! VIP and Early Entry at 5:00pm – General Admission Doors open at 5:30 PM – Event Starts at 7:00 PM Contestants Entry Fee: $20 General Admission Entry Fee: $20/$25 at the door VIP and Early Entry Options Available Tickets & Entry Fee can be purchased at thegreeenhouse.com or any Green House store. Located at Irish Kevin’s – 211 Duval Street – TICKETS
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 ‘That Hippie Band’ 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.
SINS & SEQUINS at the BLUE FLAMINGO RESORT
Step into the glamour, intrigue, and extravagance of the Jazz Age at Sins & Sequins, an unforgettable speakeasy-inspired evening during Fantasy Fest 2026 at Blue Flamingo Resort Key West. Whether you’re channeling the sultry sparkle of Roxie Hart from Chicago, the captivating allure of Sally Bowles, or the dashing sophistication of Clifford Bradshaw from Cabaret, this is your invitation to embrace the decadence of a bygone era. Slip into your finest sequins, feathers, pearls, tuxedos, suspenders, fedoras, and vintage-inspired attire for a night where glamour knows no bounds. From flappers and showgirls to gangsters and Gatsby-inspired gentlemen, Sins & Sequins welcomes everyone ready to celebrate Fantasy Fest in style. Dress to dazzle, strike a pose, and toast to a night of champagne, sophistication, and speakeasy revelry. Sequins encouraged. Glamour required. Memories guaranteed. Complimentary Parking. Blue Flamingo Resort – 3820 N Roosevelt Blvd- 7-10PM TICKETS
PARTY IN MY PANTS: A SEXY CABARET
This Fantasy Fest, the hottest party, isn’t on Duval Street. It’s in my pants and everybody’s coming! Join music icon, Johnny Showcase (America’s Got Talent Season 18), for a gloriously unhinged collision of outrageous comedy, jaw-dropping circus, and spectacular burlesque. Set to the greatest party and make-out soundtrack ever created, P.I.M.P. takes over the Key West Theater October 17 & 19 to 23 with a no-holds-barred spectacle of world-class performers, iconic songs, unforgettable moments, and enough sexy, ridiculous fun to keep the party going all night long! Tickets available at KEY WEST THEATER Doors 7:30 PM | Show 8:00 PM For more information go to PartyInMyPants.show Warning: Side effects may include spontaneous parties in your pants too.
LUV2GLOW PARTY- SPACE RAVE
Fantasy Fest’s ultimate immersive UV blacklight GLOW party returns to the heart of Key West at Rick’s Upstairs. Step into LIQUID FREQUENCY, the electrifying 2026 LUV2GLOW theme, where light, sound, and energy unite. Experience a vibrant universe of fluorescent visuals, underwater-inspired décor, and pulsating house music flowing through a world class FUNKTION-ONE sound system, delivering legendary audio all night long. Explore our expanded multi-room venue featuring immersive glowing environments, incredible performers, and a dynamic lineup of DJs: Kash (San Diego), Jevne, (MPLS), Atnarko (Orlando), The Electroniconch Crew feat: (Fikus, Elias, Ido & Zumm) Plus KW local legends Top Jimmy, Jimmy Jamz & Captain Ridiculous. : General Admission $30-$40 TICKETS Limited $100 GLOWING VIP TICKETS: (Skip to front of line, Access to exclusive VIP bar and restrooms). Door price increases the night of the event (cash only). 8:00 PM – 4:00 AM 21+. Remember NO GLOW NO ENTRY! Come dressed or painted to GLOW under blacklight. Feel the rhythm ripple through every drop of light as music becomes a living current. Flow with the frequencies, glow with the crowd, and lose yourself in an unforgettable night where sound becomes liquid and every beat radiates neon color.
MUSICAL ICONS COSTUME PARTY & KARAOKE
Jimmy Buffet’s Margaritaville Key West – 500 Duval St | 8 PM–11 PM Dress as your favorite MUSICAL ICON and then take the stage! Come dressed as your favorite singer, musician, or music legend and perform your character’s best songs during our Fantasy Fest Karaoke Night. BEST COSTUME CONTEST Great prizes will be awarded! Costumes will be judged on: Resemblance to your musical icon, Originality and creativity, Crowd participation and reaction. Plus, enjoy Fantasy Fest drink specials throughout the night! We’ll be featuring sponsored drink specials throughout Fantasy Fest, including the official Fantasy Fest Collector’s Cup Program. Grab your collector’s cup and come back for special-priced refills throughout the celebration!
THE ROCKY HORROR PICTURE SHOW
Get ready to do the Time Warp again! The Tropic Cinema is turning up the decadence for a three-night extravaganza featuring The Rocky Horror Picture Show, running October 21 through 23 at 8:00 PM nightly. Hosted by your favorite local cult leader, Landon, this isn’t just a movie—it’s a full-blown, interactive fever dream where sitting quietly in your seat is strictly forbidden. Your $45 ticket gives you the full VIP treatment, starting with a lively pre-party to mingle with fellow creatures of the night before the main event. You’ll be handed a glass of bubbles upon arrival to toast the madness, along with a custom prop bag stuffed with every gadget, noisemaker, and accessory required to throw, shout, and react right alongside the screen. Dressing up is insanely, outrageously encouraged. Dust off your fishnets, squeeze into that corset, or pull out your best golden trunks to strut your stuff for our costume showcase. Whether you’ve spent decades perfecting your Transylvanian strut or you’re an absolute virgin ready to surrender to the wildest cult classic in cinematic history, gather your crew and grab your tickets fast—because absolute pleasure is waiting, and seats won’t last long! Ages 18 and up. Strictly enforced. Buy Tickets HERE: $45 includes pre-party, prop bag, and a glass of bubbles. Tropic Cinema | 416 Eaton Street
DESIRE MALE FETISH PARTY
10PM – 4AM. Private Fetish party – For the Men. Fetish attire encouraged. Live DJ, Exhibition areas, Bring out the Gear! Free clothes check w/ $30 door cover. New Orleans House Garden & Pool Bar, Come as you are! 305-293-9800 724 Duval St. Visit us @ Bourbonstpub.com TICKETS
THURSDAY, OCTOBER 22, 2026
BERKSHIRE HATHAWAY PARADE OF HOMES MEGA OPEN HOUSE EVENT
Berkshire Hathaway Keys Real Estate | Knight & Gardner Realty invites you to a Fantasy Fest tradition, our Keys-wide Parade of Homes Mega Open House Event. Spend the day exploring a curated collection of homes from Key Largo to Key West, each with its own unique story to tell. As you tour, you’ll be entered for a chance to win four VIP tickets to our exclusive Fantasy Fest Parade Viewing Party on Saturday night. Hosted at our Duval Street office, this private event features food, drinks, and one of the best views of the official Fantasy Fest Parade. Visitors who attend three or more open houses will receive an additional entry into the giveaway. Whether you’re in the market for your dream home or simply enjoying the week’s festivities, this is a magical opportunity to see what island living is all about. For a full list of open house locations, visit their website and follow us on Facebook for updates! 11 AM – 3 PM
SOUTHERNMOST SCAVENGER HUNT’S 7th ANNUAL FANTASY FEST BAR CRAWL
Come one, come all and do the 6th Annual competitive Fantasy Fest Bar Crawl, sponsored by Dulce Vida Organic Tequila! Grab your team of up to 6 people and see if you have what it takes to bring home the grand prize! Must be 21 or older and you do not have to drink to participate. $45 per person includes the activity, the free drink, our exclusive scavenger hunt map with a value of over $160 and if you win you’ll get a lot more! Check in starts at 2:00pm and the crawl begins at 2:30pm sharp and ends at 4:30pm. Awards and winners will be announced at 5:00 pm.
FLOATAPOLOOZA
Get ready to float into Fantasy Fest at Floatapalooza, a playful beachfront celebration at The Reach Key West. Join us and come dressed in your best float-inspired attire for a day of sun, fun and Fantasy Fest flair. The festivities will feature a costume contest with multiple categories and prizes, live entertainment, and beachfront bites and refreshments available for purchase at Four Marlins Oceanfront Dining. The bigger, brighter and more creative the float, the better. | 11AM –2PM | The Reach Key West | 1435 Simonton Street.
LES GREENE & THE SWAYZEES POOL PARTY AT THE MARKER!
Get your swimsuit and come out to party with Les Greene and the Swayzees! Beyond his talent as a solo artist, Les Greene is also known for his dynamic live performances. Whether he’s commanding the stage with his soulful voice and blistering guitar solos or leading the tight-knit full band, The Swayzees through a funky groove; Greene is a consummate entertainer, capable of captivating audiences with his boundless energy and magnetic stage presence. His live shows are a testament to the transformative power of music – a shared experience that brings people together and leaves them uplifted and inspired. 2-5pm. FREE!
DANTE’S 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! Doors open at 11am, party starts at noon and goes till 6pm, pole dancing starts at 4:30 PM. Kix’ies Thigh-High Stockings and Unihorn Vibrators Raffles and Giveaways courtesy of TheTazzle.com Dante’s Restaurant & Raw Bar, 951 Caroline Street next to the ferry terminal. 305-293-5123. $20 with proceeds going to the Autism Society of the Florida Keys.
STUDIO 430 DANCE CLUB UNDER THE STARS!
Join us at our NEW pool bar and dance the evening away under the stars! Enjoy a laid-back ambiance for savoring classic cocktails and snacks. DJ Paul Allen will be bringing the tunes from 6PM-10PM. La Concha – 430 Duval Street
FUNK IT UP PARTY
Five- time Grammy Award winning funk master Trae Pierce and his T-Stone band is here to FUNK IT UP at The Green Parrot for Fantasy Fest with three sets at 5:30, 9:00 and 11:00PM. The bands’ bass drive-driven R&B/Pop blending genre bring high energy that fans have come to love. Don’t miss this party for can’t-stay-in-your-seat dance-moves and a damn good time. The Green Parrot Bar – 601 Whitehead Street – Shows at 5:30, 9:00 & 11PM – Free to watch.
GLAMOROUS DEAD & UNDEAD POPSTARS PARTY
Join us at Viva Argentinian Steakhouse for a night where the music never dies! Dress as your favorite glamorous undead popstar, legendary musician, or monstrous headliner and dance the night away with local DJs Scott Gerke & Chros Cohen spinning crowd favorites until late. Drinks will be flowing all night, and late-night eats will keep the party going. Tickets : $15 1 Drink / $60 2hs-Open Bar / $95 2hs-Open bar + Special Dinner Menu. Open Bar 6pm till 8pm. First come, First Served
STUDIO 430 DANCE CLUB UNDER THE STARS!
Where Key West Nights Come Alive. Step onto La Concha’s chic new pool deck and dance under the open sky with the island’s most stylish crowd. Sip timeless cocktails, soak up the good vibes, and let the beats move you. DJ spinning from 6–10PM | Classic cocktails • Sunset grooves • Island energy | The hottest outdoor lounge party in the heart of Key West. La Concha Hotel & Spa — 430 Duval Street
6TH ANNUAL ROCK THE TATAS CONTEST
Hank’s Hair of the Dog Saloon presents the annual charity event, Rock the Tatas contest. Join us in the fight against Breast Cancer. Our energetic event will be hosted by Mr Happy Hour Key West and DJ El Grace. Contest starts at 7pm First place price $500 along with a crown and a stash! With additional cash prices for second and third place contestants will be judge on charism, creativity and costume design. No contest entry fee. Doors open at 5pm. Tickets are $25 with a portion of the proceeds going to “Making Strides Against Breast Cancer” TICKETS Continue the party with Les Greene & The Swayzees from 9:30PM to Close. – 409 Caroline Street
DISCO FEVER COSTUME PARTY
Pull out the platforms, sequins, bell bottoms and anything else that belongs under a disco ball. We’re throwing a party at Key West Gallery and you’re invited. Join us for a night of music, great costumes, living art, drinks and plenty of fun, all inside the gallery. And the setting is pretty hard to beat. You’ll be partying surrounded by incredible fine art, including the work of world famous sculptor Bill Mack, the bold, energetic paintings of Gary Welton, known as the “Painter of Movement,” and the sculpture and collage work of Deb Mack. Dress up. Show off. Dance a little. Stay awhile. It’s Key West, it’s Fantasy Fest week and we plan on having a very good time. Key West Gallery | 601 Duval St | 7-10PM
“MOULIN ROUGE”: SING-ALONG MOVIE NIGHT IN THE COURTYARD
Adam & Eve | 524 Front Street. Join us for a free showing of Moulin Rouge under the stars in our shared courtyard. Dress to impress — prizes await the best Moulin Rouge-related costumes, and Adam & Eve will have themed costume pieces available for purchase to complete your look. The Southernmost Pint will be serving up their amazing craft beers, wine, food and more, for purchase throughout the night. Sing, dance and enjoy the show!Starts at 7:30pm.
PARTY IN MY PANTS: A SEXY CABARET
This Fantasy Fest, the hottest party, isn’t on Duval Street. It’s in my pants and everybody’s coming! Join music icon, Johnny Showcase (America’s Got Talent Season 18), for a gloriously unhinged collision of outrageous comedy, jaw-dropping circus, and spectacular burlesque. Set to the greatest party and make-out soundtrack ever created, P.I.M.P. takes over the Key West Theater October 17 & 19 to 23 with a no-holds-barred spectacle of world-class performers, iconic songs, unforgettable moments, and enough sexy, ridiculous fun to keep the party going all night long! Tickets available at KEY WEST THEATER Doors 7:30 PM | Show 8:00 PM For more information go to PartyInMyPants.show Warning: Side effects may include spontaneous parties in your pants too.
43rd ANNUAL HEADDRESS BALL
The Key West Business Guild proudly presents the 43rd Anniversary Headdress Ball, one of the most anticipated events of the Fantasy Fest celebration at the Coffee Butler Amphitheater at Truman Waterfront Park. Doors open at 6:30 PM, with the show beginning at 8:00 PM. This unforgettable evening of creativity, glamour, and entertainment will once again be hosted by legendary Key West entertainer Randy Roberts, with music by WEOW’s RudeGirl. Guests will experience an extraordinary showcase as twelve to fifteen contestants unveil their spectacular headdress creations, judged from the shoulders up—as they compete for the coveted $2,500 Grand Prize. The Headdress Ball continues to celebrate the vibrant spirit, creativity, and welcoming atmosphere that makes Key West one of the world’s most unique destinations for visitors from all walks of life. For more information, or to enter the Headdress Contest, visit gaykeywestfl.com/headdress-ball or call 305-294-4603. TICKETS
THE ROCKY HORROR PICTURE SHOW
Get ready to do the Time Warp again! The Tropic Cinema is turning up the decadence for a three-night extravaganza featuring The Rocky Horror Picture Show, running October 21 through 23 at 8:00 PM nightly. Hosted by your favorite local cult leader, Landon, this isn’t just a movie—it’s a full-blown, interactive fever dream where sitting quietly in your seat is strictly forbidden. Your $45 ticket gives you the full VIP treatment, starting with a lively pre-party to mingle with fellow creatures of the night before the main event. You’ll be handed a glass of bubbles upon arrival to toast the madness, along with a custom prop bag stuffed with every gadget, noisemaker, and accessory required to throw, shout, and react right alongside the screen. Dressing up is insanely, outrageously encouraged. Dust off your fishnets, squeeze into that corset, or pull out your best golden trunks to strut your stuff for our costume showcase. Whether you’ve spent decades perfecting your Transylvanian strut or you’re an absolute virgin ready to surrender to the wildest cult classic in cinematic history, gather your crew and grab your tickets fast—because absolute pleasure is waiting, and seats won’t last long! Ages 18 and up. Strictly enforced. Buy Tickets HERE: $45 includes pre-party, prop bag, and a glass of bubbles. Tropic Cinema | 416 Eaton Street
SLOPPY JOE’S 47th ANNUAL TOGA PARTY
Sloppy Joe’s 47th Annual TOGA! Party “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 own TOGA! using the Fantasy Fest theme “Musical Icons & Iconic Musicals”. Live music starting at 10am! Enter our costume contest & win big! 1st Place $500 Sloppy Joe’s Gift Card; 2nd Place $250 Sloppy Joe’s Gift Card; and 3rd Place $100 Sloppy Joe’s Gift Card. Sign up begins at 8:15pm next to the stage with the contest starting at 9:00pm. You may enter the contest as an individual or group of 2-4 people (Must be in TOGA! to enter the contest). “Nightbreakers” takes the Sloppy’s Stage following the contest to keep you dancing all night long! Sloppy Joe’s 201 Duval Street. #STILLTHEBESTPARTYINTOWN
EXPOSED AT THE BOURBON ST. PUB ADULT ENTERTAINMENT COMPLEX 10PM-4AM (ALL WELCOMED)
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,and exotic dancers! VIP tickets $90 presales, $100 day of event. CC sales fees will apply. Rain or Shine. Full access to the Bourbon St Pub and New Orleans House pool area, free clothes check. Limited Free towels tickets will be on sale at the New Orleans House starting September 1st; open 8 AM-8 PM. Tickets available 305-293-9800; 724 Duval Street.; Or at Keystix.com, convenience fee will apply Doors will open, 9 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.
FRIDAY, OCTOBER 23, 2026
FANTASY FEST STREET FAIR and COSTUME PROMENADE
Duval transforms into a mile-long street party of arts, eats, and island beats. Shop whimsical crafts, feast on Caribbean flavors, sip tropical drinks, and strut your costume down Key West’s most magical mile. Friday brings arts, crafts, food and music! Live entertainment by Line Dancing N’ the Keys, Mums the Word, The Fabulous Spectrelles, and Tropicado Trio! Saturday is all about the food — served up late into the night. It’s a non-stop celebration of creativity, cuisine, and pure Key West fun. Arts and Crafts : Noon – 10PM | Food : Noon – 2AM
BOURBON ST. PUB’S AFTERNOON POOL PARTY
Fantasy Fest 2025, Poolside dance party at Bourbon St Pub adult complex. Get your groove on while dancing and drinking! Live DJs, Boys, Beads and Booze, Drag Queens, games and MORE! Noon until 5 ish. $ cover charge w/FREE clothes check. Join the party at 724 Duval St. 305-293-9800.
DAY AT SOUTHERNMOST PLAYBOY MANSION – BEACH BUNNY POOL PARTY BASH
We invite you to join us at The Southernmost Mansion On The Sea, Friday, October 24th – 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: $40. 1400 Duval Street, Key West 305-296-3141; NOON-5PM.
FUNKY GRATEFUL DEAD GET DOWN PARTY & 4 DJ’s AFTER PARTY
Viva Argentinian Steakhouse | 903 Duval Street | 6PM. We are featuring a two big acts party! Starting at 6pm with a phenomenal 6-piece jam band spirit from out of town: MUMS THE WORD, they will do super funky upbeat Grateful Dead covers and more! Then at 10pm ELECTRONICONCH RECORDS will throw a very cool Afro House party with 4 Dj’s! Peace, love, funky ambience and good vibes await at the Get Down Double Party! Throw on your grooviest tie-dye, vintage band tee, or flower-power fashion and join us for an evening inspired by one of rock’s most iconic bands. Enjoy handcrafted cocktails, delicious late-night bites. LIVE MUSIC 6PM to 10PM, DJ AFTER PARTY 10PM TILL LATE. Tickets : $15 1 Drink / $60 2hs-Open Bar / $95 2hs-Open bar + Special Dinner Menu. Open Bar 6pm till 8pm. First come, First Served – TICKETS
CAPTAIN MORGAN’S MASQUERADE MARCH
Join the hugely popular Fantasy Fest tradition, known as The Locals’ Parade, highlighting costumes, creativity and community. Kick off the fun at 4PM with the Paparazzi Row Block Party at Fleming & White St— strike a pose on the red carpet, hit the 360-selfie station, and grab a cocktail before the march. 5:00 PM Keep with tradition and queue up to START with the Morganettes’ and the Band on the corner of Frances and Petronia Street. Step off at 5:30PM sharp, the Masquerade March struts through Old Town and straight into the Fantasy Fest Street Fair, with music, noisemakers, and complimentary drinks along the way. The revelry keeps rolling down Duval, then into the night at Captain Morgan’s Official Pirate After Party at Kaya Emporium or the Friday Night Fever at Hog’s Breath Saloon. Costumes, cocktails, and pure Key West chaos await! Click HERE to view the Route.
CAPTAIN MORGAN’S PIRATE PARTY
Join us at The Backyard Bar for a legendary night of rum, revelry, and high-seas mischief! This year’s pirate bash features nautical tunes and pirate shanties, a full-on costume contest, and a treasure chest of cash prizes: $500 for first place, $300 for second, and $200 for third. Whether you come as a fearless captain, a rogue buccaneer, or a siren of the seas, it’s your chance to sail into glory — and maybe leave with some loot in your pocket. Kaya Island Eats @ The Key West Empourium – 618 Duval St – 6:30PM-10:00PM – NO COVER – Bar open till 1AM
FRIDAY NIGHT FEVER AT THE HOG’S BREATH SALOON
The white suits are pressed, the platforms are polished, and Friday Night Fever hits Hog’s Breath at 7:00 p.m. on October 23rd. Channel your inner Tony Manero and hit the dance floor in your most iconic 70s disco look, whether it’s the head-to-toe white suit, the wide-open collar, platform shoes, or an afro so big it needs its own zip code – just come!!! This ain’t your average Brooklyn dance floor, but we promise it’ll feel just as electric. Our world-famous stage turns into our own version of the 2001 Odyssey Club, lit up and spinning all night with MUST SEE, MUST HEAR performers. Good energy, cold drink specials, and non-stop disco classics keeping us stayin’ alive till close. This is a FREE event. Hog’s Breath Saloon, 400 Front Street, 305-296-4222.
26th ANNUAL LIVING ART EXPO with Live Performance by Rob Benton
Witness a breathtaking showcase of the human form as a living canvas! Contestant entries are open to female, male, or group models competing for a share of $2,000 in cash and prizes, with the Best Overall walking away with $1,000 in cold, hard cash! Party Starts at 7pm. Contest begins at 8pm. Seating: Front-stage standing room and Sunset Pier table seating are completely first-come, first-served. Want to compete? For contestant registration, contact Sunset Pier at 305-295-7047 or email [email protected]. FREE to watch Ocean Key Sunset Pier – 0 Duval Street Ocean Key Sunset Pier’s Cam
PARTY IN MY PANTS: A SEXY CABARET
This Fantasy Fest, the hottest party, isn’t on Duval Street. It’s in my pants and everybody’s coming! Join music icon, Johnny Showcase (America’s Got Talent Season 18), for a gloriously unhinged collision of outrageous comedy, jaw-dropping circus, and spectacular burlesque. Set to the greatest party and make-out soundtrack ever created, P.I.M.P. takes over the Key West Theater October 17 & 19 to 23 with a no-holds-barred spectacle of world-class performers, iconic songs, unforgettable moments, and enough sexy, ridiculous fun to keep the party going all night long! Tickets available at KEY WEST THEATER Doors 7:30 PM | Show 8:00 PM For more information go to PartyInMyPants.show Warning: Side effects may include spontaneous parties in your pants too.
KINKY COUPLES PARTY HOSTED BY RUBBERDOLL!
The ONLY event exclusively for couples. Join like-minded couples in the Cabaret Bar overlooking Duval Street. A special performance by the world-renowned latex entertainer RubberDoll, including Live Dark’n Dancing. Live DJ will be sure to get everyone in the mood for some serious playtime! Doors open ten minutes before showtimes at 8PM and 11PM, Friday and Saturday. Check-in is at the ticket booth at the downstairs Bar. Private Area, Premium Open Bar, Clothes Check Couples Only! Come Together, Leave Together, Re-Entry Not Permitted, Pre-Registration Required. 801 Bourbon Bar – 801 Duval Street Shows at 8PM & 11PM – TICKETS $500 per couple.
THE ROCKY HORROR PICTURE SHOW
Get ready to do the Time Warp again! The Tropic Cinema is turning up the decadence for a three-night extravaganza featuring The Rocky Horror Picture Show, running October 21 through 23 at 8:00 PM nightly. Hosted by your favorite local cult leader, Landon, this isn’t just a movie—it’s a full-blown, interactive fever dream where sitting quietly in your seat is strictly forbidden. Your $45 ticket gives you the full VIP treatment, starting with a lively pre-party to mingle with fellow creatures of the night before the main event. You’ll be handed a glass of bubbles upon arrival to toast the madness, along with a custom prop bag stuffed with every gadget, noisemaker, and accessory required to throw, shout, and react right alongside the screen. Dressing up is insanely, outrageously encouraged. Dust off your fishnets, squeeze into that corset, or pull out your best golden trunks to strut your stuff for our costume showcase. Whether you’ve spent decades perfecting your Transylvanian strut or you’re an absolute virgin ready to surrender to the wildest cult classic in cinematic history, gather your crew and grab your tickets fast—because absolute pleasure is waiting, and seats won’t last long! Ages 18 and up. Strictly enforced. Buy Tickets HERE: $45 includes pre-party, prop bag, and a glass of bubbles. Tropic Cinema | 416 Eaton Street
MIDNIGHT MASS: A Heated GAYthering
Island House, “The Best Gay Resort in the World” since 1976, invites you to the upstairs moondeck for a night that’s anything but shy! When the sun sets over Key West, the real heat begins! Calling all daddies, jocks, bears, and every kind of gay guy in between for a night of raw attraction and unleased inhibitions! Take in the scene with low lights, deep house beats, exploring hands, and locking eyes. A masculine energy playground with big open spaces for bold moves, and dark corners for deeper connections. Massive jumbo screen, communal alters, swings, and absolutely NO judgements. Watch, play, or anything in between.…this is your night to feel the fantasy! We are a professionally produced, safe, sane, and thrilling environment where respect and consent are the only rules. Enjoy our 24hr food & bar! Admission includes your first free drink, lock & locker, towels, and resort access thru Saturday @ 4am. Photo ID required. $60 cash/credit at the door. All gay, bi, trans, queer, + brothers welcome! Party goes 10PM-2AM @ 1129 Fleming St.
SATURDAY, OCTOBER 24, 2026
FANTASY FEST STREET FAIR and COSTUME PROMENADE
Duval transforms into a mile-long street party of drinks, eats, and island beats. Feast on Caribbean flavors, sip tropical drinks, and strut your costume down Key West’s most magical mile. Saturday is all about the food — served up late into the night. From noon ‘til the early hours, it’s a non-stop celebration of delicious cuisine, and pure Key West fun!
NEW ORLEANS HOUSE POOL PARTY
Soaking Wet Pool Party / Parade day. Come splash around in the pool or jacuzzi while listening to music to get you hyped – live DJ and pool games. Join us Noon until 5pm at New Orleans House! Clothing Optional. Free clothes check w/ $20 door cover. New Orleans House Garden & Pool Bar | 305-293-9800 | 724 Duval St |
SOUTHERNMOST SCAVENGER HUNT’S 7th ANNUAL FANTASY FEST BAR CRAWL
Come one, come all and do the 7th Annual competitive Fantasy Fest Bar Crawl, sponsored by Dulce Vida Organic Tequila! Grab your team of up to 6 people and see if you have what it takes to bring home the grand prize! Must be 21 or older and you do not have to drink to participate. $45 per person includes the activity, the free drink, swag, souvenir cups, and our exclusive scavenger hunt map with a value of over $160! Winners get excellent prizes valued at hundreds of dollars! Check in starts at 2:00pm and the crawl begins at 2:30pm sharp and ends at 4:30pm. Awards and winners will be announced at 5:00 pm. For more information and tickets click HERE
BOURBON ST. PUB’S VIP BALCONY BASH
Doors open @ 6PM with a cash bar. Bash time 7PM – 10PM. Join us for one of the best views of the Fantasy Fest parade on Duval St. from the Grand Balcony. Don’t deal with the crowds! VIP high-end Top Shelf open bar and catered buffet (Mangoes Restaurant) no need to go anywhere else. Bags of Beads to toss to the crowd below! MC’d by John “Ma” Evans. Private entrance and restrooms. Don’t miss this opportunity for a great vantage point to see the parade and a fantastic party. VIP presale Tickets $200. No reserved spaces, first come, first served. Only 150 tickets available! Tickets on sale September 1 at the New Orleans House or ONLINE 305-293-9800 | 724 Duval Street | Open 8AM – 8PM
FIRST FLIGHT PARADE VIEWING PARTY
Enjoy all the parade Extravagance from the comfort of First flight Island Restaurant & Brewery. Saturday, October 24, 2026, 6-9 pm (5:30pm check-in) ALL Tickets include: Signature Dinner Buffet and 3-hour Open Bar! 3 Ticket Options: $125++ Sidewalk Chair ticket: Seating is First come, First serve. Guests are asked to check in with the hostess and receive a name card for the sidewalk chair. Then we would like to invite you to enjoy your meal, open seating, family style in the Canopy Garden! This will allow everyone to enjoy cocktails, food, and festivities for about an hour and then 7:00 pm is PARADE time!!! $150++ Indoor Table ticket: Reserved table seating for you and your friends, inside our air-conditioned dining room with the doors open for the parade view. Also, includes a designated porch for standing. $150++ Downstairs Porch Chair ticket: Front porch seating area just up from the sidewalk! Very Limited! $200++ High Top Table for Two:Reserve your own private high-top table for two, perfectly positioned to enjoy the parade, cocktails, and dinner in comfort. This exclusive option includes all event amenities and offers a more intimate viewing experience. TICKETS
MANGOES FANTASY FEST PARADE PARTY
Join us a step above Duval with all the comforts of home for one of the most epic parties of the year. Mangoes Private Parade Party offers an elevated patio for street spectating, incredible drink specials, an air-conditioned dining option, and a special parade party dinner menu for purchase. After the parade, stay and enjoy live entertainment by island legend piano player Dave Bootle! Pre-purchase your tickets starting at $90 for presale and $100 the day of the event at the door. Doors open at 6 PM. Parade to start at 7 PM.Tickets grant you access to the private event, the entire ground floor of the restaurant and bar area, air-conditioned bathrooms, and an air-conditioned dining room. Please arrive early to secure a seat up front; space is first-come, first-served, and we cannot accept reservations. TICKETS
STUDIO 319 – PARTY LIKE A ROCKSTAR – Fantasy Fest Parade Viewing Party
For one night, 319 Duval goes full rockstar! Dress as your favorite music icon, enter through our private gate, pass the velvet ropes, and step into Studio 319. Grab a cocktail, take your reserved seat in our courtyard, and watch the Fantasy Fest Parade in first-class style from the heart of historic Duval Street. Your ticket includes reserved courtyard seating, a chef-prepared gourmet buffet, handcrafted signature cocktails, sparkling clean private restrooms, and an exclusive VIP celebration behind the gates of one of Key West’s most iconic historic homes. 6:00-10:00PM – 319 Duval Street – Hellings Curry Museum Key West Woman’s Club. $350.00 per guest.Tickets are limited—and this event sells out every year. TICKETS
VIP PARADE VIEWING PARTY AT THE NEW SMOKIN TUNA!
Smokin Tuna is back—and there’s no better way to celebrate than with a VIP view of the Fantasy Fest Parade! Enjoy the action from the patio with dinner, drinks, and a front-row seat to the spectacle rolling down Duval Street. Tickets start at $300 per person, including dinner and a drink. 313 Duval St | 6–10 PM – Purchase Tickets HERE
VIVA’S GRAND FINALE VIEWING & DINNER PARADE PARTY
Viva Argentinian Steakhouse | 903 Duval Street | 6P-1130PM (5PM check-in). The coolest private parade party on the island. Viva’s offers a large outdoor seating, large outdoor tiki bar, large air-conditioned inside bar viewing option, live music and DJ party. vegetarian-vegan option by request. First come, First Served. Tickets :$80 2hs-Open Bar / $145 2hs-Open bar + Special Dinner Menu. Open Bar 6pm till 8pm. TICKETS
DEEP EDDY VODKA FANTASY FEST PARADE
Join 70,000 exuberant partygoers as this year’s Key West 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 Web Cams
PARADE VIEWING PARTY AT LA TE DA
Join the Fun at La Te Da – Street side for a front row view with our favorite MC Rude Girl – from WEOW 92.7 who will be on hand to celebrate with you and announce all the fabulous floats, and walking groups in the Fantasy Fest Parade! 1125 Duval Street | 6-10pm
KINKY COUPLES PARTY HOSTED BY RUBBERDOLL!
The ONLY event exclusively for couples. Join like-minded couples in the Cabaret Bar overlooking Duval Street. A special performance by the world-renowned latex entertainer RubberDoll, including Live Dark’n Dancing. Live DJ will be sure to get everyone in the mood for some serious playtime! Doors open ten minutes before showtimes at 8PM and 11PM, Friday and Saturday. Check-in is at the ticket booth at the downstairs Bar. Private Area, Premium Open Bar, Clothes Check Couples Only! Come Together, Leave Together, Re-Entry Not Permitted, Pre-Registration Required. 801 Bourbon Bar – 801 Duval Street Shows at 8PM & 11PM – TICKETS: $500 per couple.
THE BLUE PARTY AT THE BACKYARD BAR
Dive into a sea of music, color, and ocean vibes at this year’s Blue Party! The theme is simple: the color blue and the magic of the ocean. Come dressed as your favorite creature of the sea, from mystical mermaids to deep-sea divers, and let the waves of creativity roll. Jeff Clark’s All Star Band will keep the night flowing with timeless blues classics, setting the perfect soundtrack for an unforgettable evening. With partial proceeds supporting Sea Basecamp, every splash of fun helps protect the waters we celebrate. Kaya Island Eats @ The Key West Empourium | 618 Duval St | Party starts a@ 8PM and goes all night!
SUNDAY, OCTOBER 26, 2025
FANTASY PICKLEBALL TOURNAMENT
Join us at Higgs Beach Pickleball Courts from 8am-11:30am on Sunday, October 26th. Your $100 Donation gets you a continental breakfast, fun pickleball, an original KEY WEST PICKLEBALL hat or visor, awards and a great lunch afterwards. All this to help support Keys to Be the Change Mentoring Programs. Keys to Be the Change is a grassroots, non-profit organization that provides programs, education, awareness and opportunities that empower children, youth and adults to improve health, wellness and skills for success in school and in life. Our programs include the Kids Win Mentoring Program & the MORE Literacy Initiative. Call/Text/Email to sign up 541-974-4398 or [email protected]. Please visit our Website to learn more about what we do for our community. Registration is limited to 40 people. Bring a partner or we can match you up!
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.
BOWTIES & BIRTHDAY SUITS!
Island House, “The Best Gay Resort in the World” since 1976, invites you to an EPIC, gay men’s clothing-optional pool party! All body types are welcome and absolutely NO costumes needed! Mingle and frolic while rocking your bowtie alongside other like-minded guys in the pool, indoor & outdoor Jacuzzis, and steam room! Great music, videos, and friendly pool boys. 24hr food & bar! Admission includes one Bowtie, lock & locker, pool towels, and resort access thru Monday @ 4am. Photo ID required. $50 cash/credit at the door. All gay, bi, trans, queer, + brothers welcome! Party goes 12-4PM @ 1129 Fleming St.
REGGAE REHAB POOL PARTY WITH CHANNEL 3
One of Key West’s most established and chill vibe trio, Channel 3, lead by seasoned drummer Ray Spence, along with Dirty Monkey Banana Peanut Butter Whiskey specials, Deep Eddy Bloody Bar, and more, will help whisk away your hangover blues – reggae style. Sunday, 10/25, 1-4pm, The Marker. FREE!
THE HANGOVER “BUT DID YOU DIE?” POOL PARTY AT SOMO’S PINEAPPLE POOL
You bring your inner Mr. Chow, Alan, Stu, or anyone else from the Hangover gang, and we’ll bring plenty of food, drink specials and swag by Dirty Monkey Banana Peanut Butter Whiskey, and a live DJ spinning all your favorites including “Allentown” We’ll also have $10 Deep Eddy’s Bloody Mary specials, of course. Sunday, 10/25, 1-4pm Southernmost Beach Resort’s Pineapple Pool. 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. 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
For more information about things to do and see in our island city, go to our Key West Web Site. You can also visit our Key West Events Calendar to see upcoming special events.
And for more restaurant reviews check out our restaurant review section of this blog as well as our restaurant reviews at www.gotothekeys.com.
Island Genn – Your Key West Concierge
