Bourbon St Pub's VIP Balcony Bash
Join us for one of the best views of the Fantasy Fest parade on Duval St. from the Grand Balcony of the New Orleans House, 724 Duval St. Don't deal with the crowds! VIP high-end 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.
Mangoes Fantasy Fest Parade Party
Join us a step above Duval Street for one of the most epic parties of the year! Mangoes Private Parade Party puts you right in the heart of the action with an elevated patio for prime parade viewing, incredible drink specials, air-conditioned indoor space, and a special parade-night dinner menu available for purchase.
STUDIO 319 - Party Like a Rockstar
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.
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 with live DJ and pool games.
Join us 12 Noon until 5pm at New Orleans House! Clothing Optional.
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!
Bourbon St Pub's Afternoon Pool Party
Fantasy Fest 2026, Poolside Dance Party / Street Fair T Dance at the Bourbon St Pub Adult Complex.
Get your groove on while dancing and drinking at the Duval Street T Dance or Poolside at the Bourbon St Pub! Live DJs, Boys, Beads and Booze, Drag Queens, games and MORE! 12 noon until 5-ish.
Exposed
10PM-4AM - Event Open to All! The most risqué party of Fantasy Fest! Voyeur/Exhibition areas throughout! Play in the Poolside Foam Party!
Dance the night away w/DJ Gyvers/outdoor Laser Light show, Splash around in our Pool & Jacuzzi! Black Out & Black Light party inside, TheTazzle.com will be there adding some extra excitement with fun giveaways of OXJOK and more!
43rd Anniversary of the Headdress Ball 2026
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 stunning Headdress creations, judged from the shoulders up, all competing for the coveted $5,000 grand prize. The evening will also feature performances by some of Key West’s most celebrated local talent, making this a true highlight of Fantasy Fest. Guests can enjoy full bar service, specialty wines, and the convenience of preordered food delivered directly to their tables.
6th Annual "Rock the Tatas"
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 at Hanks Hair of the Dog Saloon located at 409 Caroline St. 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
Desire Male Fetish Party
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.
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.
Fantasy Fest Spooky Trivia
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! $25, including your first spooky drink!
Tops or Bottoms Underwear Party
Underwear party 10PM - 4AM.
Private Underwear party - For the Men, You must lose one or the other or both!
Free clothes check w/ $20 door cover.
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
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.
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.
2026 What I Did Fur Love Royal Coronation
Join the Florida Keys SPCA at the 2026 What I Did Fur Love 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 2026! This fabulous 2-hour stage show includes entertainment by local celebrities and the candidates themselves!
Tickets include reserved seatingand a 3-course plated dinner by Catered Affairs (vegan meal available upon request - please email Jennifer@fkspca.org to order in advance). Cash bar for all.
Barbie's Pink Pool Party for Breast Cancer Awareness
Wear your Best Barbie or Ken pink costumes and join The Marker Key West Harbor Resort along with a fun pool party that will also make you feel good! Along with great music by DJ Top Jimmy and DJ Maya, we'll have a Barbie or Ken costume contest, Barbie pink pools, Barbie pink drink specials by Empress Gin, pink food specials, and more – all to benefit Womankind Key West.
HANGOVER POOL PARTY AT SOMO'S PINEAPPLE POOL
We'll have plenty of food and drink specials, and a live DJ spinning all your favorites, Deep Eddy’s Bloody Mary specials
CHANNEL 3 AND REGGAE LOU & THE KIND BUDZ REHAB POOL PARTY, LIVE AT THE MARKER
Sponsored by Dirty Monkey Banana Peanut Butter Whiskey, this will be a rehab party for the books, as well as to cure your Fantasy Fest hangover! Channel 3 and Reggae Lou & The Kind Budz will have your vibes flowing with their hit, “Key West It Is The Best”, and more! Dirty Monkey drink specials, two pools, and plenty of hungover people watching! FREE! Noon to 5pm. Reserve your spot
Bourbon St Pub's VIP Balcony Bash
Join us for one of the best views of the Fantasy Fest parade on Duval St. from the Grand Balcony of the New Orleans House, 724 Duval St. 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.
Nightcaps & Nightgowns
A Moonlight Pajama Party Parade Viewing Experience
One night. One view. One unforgettable pajama party.
Kinky Couples Party
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. New York DJ Lucas will be sure to get everyone in the mood for some serious playtime!
Exposed Party
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! Rain or Shine.
42nd Anniversary Headdress Ball 2025
Popular Key West entertainer, Randy Roberts will emcee and arrange the show this year. WEOW’s Rudegirl oversees the music. Twelve to Fifteen contestants will hit the stage to show their Headdress creations, judged from the shoulders up, and vie for the first prize of $5,000. Performances by some of Key West’s best local talent from over the years will again be featured. There is bar service and specialty wine; food may be preordered and delivered to your table. Tickets are $320 for a premium table of 4, $270 for a VIP table of 4, with Chair seating at $35 and General Admission (grass seating) at $30.
Kinky Kandyland
Join us for an electrifying candy-themed party with fantasy drinks, glowing lights, two stages, three bars, and a live DJ. Indulge in candy martinis, ice cream, cotton candy, and more. Sweet, wild, and totally unforgettable. Guests are encouraged to go all out with bright colors, glitter, latex, feathers, LED accents, and over-the-top accessories that fit the candyland fantasy vibe.
5th Annual "Rock the Tatas"
Hanks’ Hair of the Dog Saloon presents the annual charity event, Rock the Tatas Contest. Join us in the fight against Breast Cancer October 23rd. Our energetic event will be hosted by the lovely Kirby Myers and DJ Sanaris. Live music afterwards from 9pm to close. Contest starts at 7 PM at Hanks Hair of the Dog Saloon located at 409 Caroline St. First place prize $500 along with a Crown and Sash! With additional cash prizes for second place. Contestants will be judged on Charism, Creativity, and Costume design
LES GREEENE & THE SWAYZEES PAJAMA POOL PARTY TAKE 2 AT THE MARKER!
Get your swimsuit or your PJs (or both!) and come out to party with Les Greene and the Swayzees! Sponsored by Dulce Vida Organic Tequila. 2-5pm.
PAST YOUR BEDTIME: A Surreal Extravaganza
Transforming 801 Bourbon Bar + Upstairs Cabaret + Saloon 1
LIVE MUSIC ORIGINAL ART LOCAL TALENT CIRQUE BURLESQUE DRAG COMMEDIA DELL'ARTE * LIVE ENTERTAINMENT ALL NIGHT LONG
The Hush Hush Theatre is a pop-up theatre exploring new realms of storytelling through live music, dance, burlesque, drag, comedy and cirque. We encourage new talent, original work and the unconventional.
32nd Annual Homemade Bikini Contest Presented by Rancho Relaxo
Irish Kevin’s is proud to present the 32nd Anniversary of the Original Key West Homemade Bikini Contest. 7PM CONTEST. Over $2,500 in cash & prizes. Creativity and attention to detail are the key elements to winning the 1st place prize of $1000. Additional cash prizes for 2nd & 3rd place. Hosted by the World-Famous Emcee and Local Celebrity Mr. Bill Hoebee and his celebrity judges.