Fantasy Fest Wednesday | 2025
October 22, 2025 • Key West Tourist
Fantasy Fest Wednesday: Pet Masquerade, Wharfstock & Bikini Contest in Key West
Fantasy Fest 2025 continues tonight, Wednesday, October 22, with an imaginative “Bedtime Stories & Magical Monsters” theme inspiring costumes across the island. From playful pool parties to classic Fantasy Fest traditions, Key West transforms into a whimsical wonderland of creativity and celebration.
Swayzees Pajama Pool Party at Southernmost Beach Resort (2:00–5:00 PM) kicks off the afternoon with high-energy live music by Les Greene & The Swayzees. Guests can splash, dance, or relax poolside in pajamas, swimsuits, or a combination of both.
At 6:00 PM, the resort keeps the fun rolling with Spooky Trivia, where costumes are encouraged and teams compete for prizes. Early reservations are recommended as tables fill fast.
The Pet Masquerade at the Coffee Butler Amphitheater (6:30 PM) is a family-friendly favorite where costumed pets—furry, feathered, or scaly—strut their stuff in categories including Best Theme, Most Exotic, and Best in Show. Entry registration begins at 5:00 PM, and spectators enjoy free admission with lawn seating available on a first-come basis.
For the adult crowd, Irish Kevin’s hosts the 32nd Annual Homemade Bikini Contest (7:00 PM), offering over $2,500 in cash and prizes, including a $1,000 grand prize. Hosted by Bill Hoebee, the contest draws a lively crowd and features a panel of celebrity judges.
Meanwhile, the Schooner Wharf Bar brings back its beloved Wharfstock Party (7:00 PM–Midnight), a ‘60s-themed tie-dye celebration of “Peace & Love.” Enjoy live music from That Hippie Band and a costume contest around 8:30 PM.
Visitor Tips:
Plan to arrive early for popular events such as the Pet Masquerade and Bikini Contest, and bring a folding chair or blanket for outdoor shows. Costumes that embrace the “Bedtime Stories & Magical Monsters” theme—like pajamas, fantasy creatures, or dreamy bedtime characters—fit right in. Utilize the Duval Loop shuttle to move easily between venues, and note that some events are 21+ only.
