Wear your Best Barbie or Ken pink costumes and join The Marker Key West Harbor Resort 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!

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!

Sponsored by Empress Gin – wear your dead Dr. or Nurse costume and join us at the transformed Avalon Guesthouse (Haunted Hospital), 1317 Duval Street, for the best spot to watch your fellow dead ride by for the Zombie Bike Ride. We’ll have drink specials all night, including the Blood Bag cocktail! 6-9pm, Avalon Guesthouse

Step into Afterlife: The Seduction, an erotic kickoff to Fantasy Fest at Bourbon St. Pub Garden. This immersive night features aerial burlesque over the pool, voyeur shower stations, body paint games, and sensual performances designed to tease every sense. From the temptation of shadowplay to the energy of the main stage, this forbidden garden delivers the unforgettable experience Fantasy Fest is known for.

Step into an evening of mystery and elegance at our Bridgeton-inspired Masquerade Ball Wine Tasting Dinner featuring Juggernaut 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.

Once upon a time… the heroines stopped behaving, the villains got seductive, and bedtime stories were rewritten under the glow of candlelight and cocktails. Join us for a decadent night of mystery, mischief, and magic, where fairy tales go rogue and the monsters under the bed are invited in for a drink. ✨ Dress as your inner Vixen or Villain—a wicked queen in velvet, a dreamy siren in silk, a seductive beast from the shadows. Whether you come draped in lace or crowned in horns, your fantasy is welcome here.

You will enjoy two rum Tastings of Captain Morgan White and Spiced Captain Morgan. Followed by two rum cocktail samples and two rum drinks that you personally make and enjoy. During this experience, you will learn the history of these rum drinks as well as a bit of background on Captain Morgan and what makes their rum so amazing. With this special Fantasy Fest Captain Morgan Cocktail Class, you will receive a swag bag filled with fun goodies to enjoy!

In honor of Tutu Tuesday, join us at the Southernmost Beach Café for a fun evening of Salsa dancing while wearing your tutus. Instruction by Salsa John, sponsored by Dulce Vida Organic Tequila. Enjoy margarita and sangria specials while you dance your tutus off 7-9pm, Southernmost Beach Resort

Grab your PJs or your swimsuit (or both) and come dance, swim and drink with Les Greene and the Swayzees!

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.

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.

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. 

Get your swimsuit or your PJs (or both!) and come out to party with Les Greene and the Swayzees!

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!

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.

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.

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!

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.

A Moonlight Pajama Party Parade Viewing Experience

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.

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.

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!

We'll have plenty of food and drink specials, and a live DJ spinning all your favorites, Deep Eddy’s Bloody Mary specials. Sunday, 10/25, 1-4pm Southernmost Beach Resort’s Pineapple Pool. FREE! Reserve your space