Fantasy Fest Thursday | 2025
October 23, 2025 • Key West Tourist
Fantasy Fest Thursday 2025: Pool Parties, Parades & Pure Key West Mayhem
By Thursday, October 23, 2025, the island of Key West is in full Fantasy Fest fever — a cocktail of sunshine, costumes, and carefree fun where the theme “Bedtime Stories & Magical Monsters” plays out across every pool deck and dance floor. It’s the day when flip-flops meet feathers, and margaritas mingle with mischief from sunrise to last call.
Afternoon Antics: Pool Parties & Bar Crawls
When the sun hits high and the streets start to shimmer, Key West turns into one giant playground of beats, bikinis, and tequila.
Les Greene & The Swayzees Pajama Pool Party at The Marker Resort
From 2 PM – 5 PM, the soulful energy of Les Greene & The Swayzees turns The Marker’s waterfront pool into a tropical stage. Expect rock, rhythm, and Dulce Vida Organic Tequila flowing as partygoers show off their best pajama or swimsuit looks. This one’s a can’t-miss afternoon of live music and pure island groove.
Southernmost Scavenger Hunt Bar Crawl
At 2 PM, the 6th Annual Fantasy Fest Bar Crawl kicks off check-in, with the crawl beginning at 2:30 PM. For $45 per person, teams of up to six navigate Duval Street’s hottest bars on a hilarious, slightly buzzed treasure hunt, earning prizes, swag, and eternal bragging rights by 5 PM.
Halos & Horns Pool Party at Dante’s Restaurant & Raw Bar
From Noon – 6 PM, Dante’s transforms into the island’s most decadent splash zone for the 19th Annual Halos & Horns Pool Party. Dive into live music, body painting, and a stage suspended above the pool. Whether you’re feeling angelic or naughty, this Fantasy Fest classic benefits the Autism Society of the Florida Keys. $25 admission keeps it charitable and chaotic.
Evening Escapades: Costumes, Charity & Cocktails
As the sky blushes orange over Mallory Square, the island shifts from sunscreen to sequins.
42nd Annual Headdress Ball at Coffee Butler Amphitheater
Starting at 8 PM, the Key West Business Guild hosts this legendary showcase of creativity and color. Hosted by Randy Roberts with music by DJ Rudegirl, contestants compete for $5,000 in prizes with feathered, glittering masterpieces that defy imagination. Reserve tickets at KeyStix.com for one of Fantasy Fest’s most glamorous nights under the stars.
Rock the Tatas at Hank’s Hair of the Dog Saloon
At 7 PM, Hank’s (409 Caroline Street) turns pink for a purpose. Hosted by Kirby Myers & DJ Sanaris, this upbeat breast cancer awareness fundraiser features live entertainment and a $500 prize plus crown for the Rock the Tatas champion. $25 tickets benefit Making Strides Against Breast Cancer.
Studio 430 Dance Club Under the Stars at La Concha Hotel
For a touch of class, La Concha Hotel (430 Duval Street) hosts an open-air pool deck dance party from 6 PM – 10 PM. Classic cocktails, moonlit beats, and a skyline view make it one of the most elevated Fantasy Fest events of the night.
Late-Night Legends: Duval Street After Dark
When the stars come out, Key West lets loose.
Sloppy Joe’s 46th Annual Toga Party
At 201 Duval Street, the original Fantasy Fest bash gets wild. Sign-up at 8:15 PM, contest at 9 PM, and The Nightbreakers rock the stage all night long. Whether you go classic white sheet or something creatively scandalous, this toga tradition never disappoints.
Fat Tuesday Pink Party
From 8 PM to close, Fat Tuesday (305 Duval Street) turns bubblegum pink with DJs, daiquiris, and $500 in bar tab prizes for the boldest costumes.
Kinky Kandyland at Sugar Shack
A candy-coated, glow-lit fever dream begins at 7 PM at 221 Duval Street. $25 advance / $35 day-of, and the dress code? Glitter, feathers, and LED fantasy — the sweeter, the better.
Cowboys, Cowgirls & Monsters at The Alamo
Over at 4 Charles Street, The Alamo blends western grit with Fantasy Fest weirdness. DJs Scott Gerke & Chros Cohen spin from 7 PM on. $15 entry, $45 open bar, or $75 with dinner — pick your poison.
Exposed at Bourbon St. Pub
From 10 PM – 4 AM, Bourbon St. Pub (724 Duval Street) brings the heat with blacklights, foam, and two dance floors. VIP tickets $100 presale / $110 day-of guarantee a night of unfiltered Key West energy.
Irish Kevin’s 80’s Party
Close out the night at 211 Duval Street with Irish Kevin’s no-cover 80’s blowout, featuring live bands, neon lights, and enough nostalgia to power a DeLorean.
A Toast to Thursday in Paradise
By the end of the night, Duval Street glows like a carnival caught in a sunset. Thursday at Fantasy Fest 2025 captures everything the island stands for — music, mayhem, and a little bit of magic in every margarita. From poolside splashes to dance floor clashes, this is Key West at its absolute best.
