We'll have plenty of food and drink specials, and a live DJ spinning all your favorites, Deep Eddy’s Bloody Mary specials

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. 

A Moonlight Pajama Party Parade Viewing Experience

One night. One view. One unforgettable pajama party.

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.

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.

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

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.

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 1^st 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.

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!

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

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

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!

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!

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.

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.

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.

A flavorful fundraiser for Floyd “Pepa” Jenkins, candidate for Fantasy Fest King 2025, benefiting the Florida Keys SPCA 🐾

👨‍🍳 Featuring:

• Chef Joey Bove (“Salt”)

• Floyd Jenkins (“Pepa”)

• Resident Chef Karl from the Key West Cooking School
  

A pool party concert to wrap up the week’s debauchery, not to be missed!

We'll have plenty of food and drink specials, and a live DJ spinning all your favorites, along with free Booze Bandages for the first 50 guests, to bring you back to life! Deep Eddy’s Bloody Mary specials.

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.

Watch the Fantasy Fest Parade from one of Key West’s best locations! Tickets include a seated three course dinner at decorated tables and two complimentary drinks at the gorgeous courtyard or porch of the historic Hellings Curry Museum.