Fantasy Fest Key West 2025: Bedtime Stories & Magical Monsters
Let the countdown begin. Fantasy Fest 2025 takes over Key West, Florida from October 17 to 26, bringing a costume extravaganza of creativity, chaos, and unforgettable fun. Locals and visitors alike turn their wildest ideas into reality, filling the island with one‑of‑a‑kind looks and nonstop celebration. This year’s theme, “Bedtime Stories & Magical Monsters,” sets the stage for fairy‑tale characters, creatures that go bump in the night, and plenty of surprises no one could script. From the lively Goombay Festival kickoff to the grand Deep Eddy Vodka Parade finale, the festival delivers ten days of parades, parties, and round‑the‑clock revelry stretching from the Historic Seaport to South Beach. Photo by Nick Doll.
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, with bar crawls, pop-up parties, and a pre-parade across the Caroline Street district, plus 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.
Photo courtesy of Fantasy Fest
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.
Photo by Larry Blackburn
Wait, there’s more. Captain Tony’s Party in Plaid, Fat Tuesday’s Pink Party, Irish Kevin’s 80s Party, Sloppy Joe’s legendary Toga Party, a homemade bikini contest, and Wharfstock, peace and love, Woodstock style at Schooner Wharf Bar. And that’s just the start. Download the official Fantasy Fest app and keep the official Fantasy Fest schedule handy for live updates to dates, times, tickets, and venues
Fantasy Fest Resort Events
Fantasy Fest spills beyond Duval Street, and some of the best parties happen by the beach and poolside at Southernmost Beach Resort and at our sister property, The Marker Key West Harbor Resort by the Historic Seaport. Here’s what’s on the lineup this year:
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.
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.
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 Fantasy Fest fun by the beach, at the pool, and on Duval, we’ve learned the best stories start with “So there we were at Fantasy Fest.” Tell us your story. #somolife