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 Wes

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 seating and a 3-course plated dinner by Catered Affairs. Cash bar for all.

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.

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.

FREE!

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.

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.

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

FREE!

Get your swimsuit or your best Madonna or Bowie gear (or both!) and come out to party with Les Greene and the Swayzees, and Dulce Vida Tequila!

FREE!

In honor of Tutu Tuesday, join us at the Southernmost Beach Café for a 2hr max. $22 bottomless mimosas throughout the day, and a fun evening of Salsa dancing while wearing your tutus. Instruction by Salsa John, sponsored by Dulce Vida Organic Tequila and Bogle Family Vineyards.

Enjoy margarita and sangria specials while you dance your tutus off!

FREE!

Brought to you by Empress Gin - Grab your best Freddie Mercury or Madonna gear or your swimsuit (or both) and come dance, swim and drink with Key West’s favorite, 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; tables will fill fast!

Get ready to do the Time Warp again!

The Tropic Cinema is turning up the decadence for a three-night Halloween 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.

Fetish Party 10PM - 4AM.

Private Fetish party - For the Men,  Fetish attire encouraged. Live DJ, Exhibition areas, Bring out the Gear!

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.

Get ready to do the Time Warp again!

The Tropic Cinema is turning up the decadence for a three-night Halloween 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.

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.

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!

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!

Get ready to do the Time Warp again!

The Tropic Cinema is turning up the decadence for a three-night Halloween 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.

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 8:00 and 11:00pm, Friday and Saturday.

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.

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.

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.

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. 

FREE!

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.

FREE!

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.