October 01, 2025

Photo by Larry Blackburn

Are you ready for it? We are, and we can’t wait, because every October, Key West transforms into ten days of pure creative chaos as Fantasy Fest takes over the island. From October 17 to 26, 2025, locals and visitors alike bring their wildest costume ideas to life in a one-of-a-kind celebration. This year’s theme, “Bedtime Stories & Magical Monsters,” sets the stage for everything from fairy tale characters to creatures that go bump in the night. With parades, parties, and round-the-clock revelry stretching from the Historic Seaport to South Beach, one thing is certain: one costume is never enough.

Spotlight on Can’t-Miss Fantasy Fest Events

Goombay Festival (October 17–18, 2025)
Two-day street party in Bahama Village with live music, Caribbean food, and family-friendly fun celebrating Bahamian heritage.

Zombie Bike Ride (October 19, 2025)
Thousands of costumed zombies ride at sunset from the Atlantic shoreline into Old Town, ending with a street party.

Tutu Tuesday (October 21, 2025)
This is now a Tuesday tradition where tutus take over Old Town, featuring bar crawls, pop-up parties, and a pre-parade across the Caroline Street district, along with TuTu Salsa Sessions at Southernmost Beach Cafe.

Pet Masquerade (October 22, 2025)
Pets and their people hit the stage in imaginative costumes for one of the festival’s most beloved traditions.

42nd Annual Headdress Ball (October 23, 2025)
Extravagant headdresses and dazzling performances light up Truman Waterfront Park. Always a sellout event, so plan ahead.

Captain Morgan’s Masquerade March (October 24, 2025)
Known as the Locals’ Parade, this free-spirited walking parade winds through Old Town with costumes, music, and spontaneous party stops.

Deep Eddy Vodka Fantasy Fest Parade (October 25, 2025)
The grand finale on Duval Street. Floats, costumes, and marching groups fill the island in one unforgettable night of celebration.

And that’s just the start. Download the official Fantasy Fest app and check the official Fantasy Fest schedule for live updates to dates, times, tickets, and venues. Beyond these highlights, the week is packed with themed parties like Sloppy Joe’s Annual Toga Party, Wharfstock at Schooner Wharf Bar, and dozens more that keep the island buzzing from morning until late night. Everywhere you turn, there’s another costume contest, live music, and a party happening.

Fantasy Fest Resort Events

Fantasy Fest spills beyond Duval Street, and some of the best parties happen poolside at The Marker Key West Harbor Resort by the Historic Seaport and at our sister property, Southernmost Beach Resort. Here’s what’s on the lineup this year:

The Marker Key West Harbor Resort

Friday, October 17 - Barbie Pink Pool Party for Breast Cancer Awareness | 4 to 7 PM | $20 donation | DJ Top Jimmy, Barbie & Ken costume contest, photo booth, pink drink and food specials. Proceeds benefit Womankind Key West. Wear pink!

Thursday, October 23 - Les Greene & The Swayzees Pajama Pool Party Take 2 | 2 to 5 PM | Free | Get your swimsuit, your PJs, or both, and come party with Les Greene and The Swayzees. Known for their high-energy live shows, this is a performance you don’t want to miss. Sponsored by Dulce Vida Organic Tequila.

Sunday, October 26 - Channel 3 and Reggae Lou & The Kind Budz Rehab Pool Party | 2 to 5 PM | Free | Sponsored by Dirty Monkey Banana Peanut Butter Whiskey, this “rehab party for the books” will help cure your Fantasy Fest hangover. Channel 3 and Reggae Lou & The Kind Budz keep the vibes flowing poolside with favorites like “Key West It Is The Best.” Enjoy Dirty Monkey drink specials and an afternoon of fun.

See all Marker Fantasy Fest events on KeysTix.

Southernmost Beach Resort

Sunday, October 19 - Dead Doctors & Nurses Haunted Hospital Zombie Watch Party at the Avalon Guesthouse | 6 to 9 PM | Free | Hosted by Empress Gin. Dress as a doctor or nurse with a haunted twist and watch the Zombie Bike Ride from the transformed Avalon Guesthouse (Haunted Hospital). Themed drink specials all night, including the Blood Bag cocktail.

Tuesday, October 21 - TuTu Salsa Sessions at Southernmost Beach Cafe | 7 to 9 PM | Free | Wear your tutu and dance salsa by the sea with instructor Salsa John. Margarita and sangria specials sponsored by Dulce Vida Organic Tequila.

Wednesday, October 22 - Swayzees Pajama Pool Party at SoMo’s Shores Pool | 2 to 5 PM | Free | Grab your PJs or your swimsuit (or both) and come dance, swim and drink with Les Greene and the Swayzees!

Sunday, October 26 - Hangover Pool Party at the Pineapple Pool | 1 to 4 PM | Free | DJ spinning favorites, food and drink specials, including Deep Eddy’s Bloody Mary bar. The perfect spot to recover and toast the end of Fantasy Fest.

See all Southernmost Beach Resort Fantasy Fest events on KeysTix.

Pro Tips for the Perfect Festival

● Download the Fantasy Fest app to keep track of schedule updates, venues, and ticket info on the go.

● Get creative with costumes and have fun with the theme

● Plan ahead and know what’s happening when

● Pace yourself and hydrate

● Wear comfortable shoes

● For a deeper dive into planning, packing, and insider hacks, check out our tips for an unforgettable festival experience.

Planning flights to Key West? Read our 2025 Fall Air Travel Updates for airline tips and nonstop route options into EYW.

After years of hosting Fantasy Fest guests, one truth stands out: the best stories always begin with “So there we were at Fantasy Fest.” We can’t wait to hear yours. See you soon! #lovethemarker

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