Fantasy fest key west gay
Ernest Hemingway wrote, “Everyone behaves badly — given the chance.” Yes, old Ernie must have been talking about Fantasy Fest in Key West.
The southernmost island of everyone’s favorite archipelago consistently lures travelers year-round. With its come-as-you-are spirit, tropical atmosphere, beautiful landscaping, crystal water and clothing-optional attitude — what’s not to love? Key West means happiness.
Always ready for a party, Cuba’s tiny neighbor amps it up during Fantasy Fest, a day, no-holds-barred fête filled with costumes, body coat, drinking, dancing, life loving and skin aplenty. I consider it a tall holy day (lowercase; no offense here!) and verb south for it every year, meticulously planned outfits in tow. The celebration — themed Its a 90s Neon Cosmic Carnival! for — is going down later this month from October 18–27,
Headed to the bash? Still thinking about going to the party? Here are the highlights. Cant create it? Keep scrolling down to the anytime suggestions for your off-Fest Key West getaway.
Fantasy Fest Highlights for Gay Men
Zombie Bike
Don’t be fooled by its size: Tiny Key West knows how to pitch a big party, and the LGBTQ community puts on some of the best. From Carnival-style fêtes to gown-clown extravaganzas, the island’s panoply of queer festivals celebrates all members of the alphabet mafia throughout the year.
Plan your next Florida getaway around one of these eight events, when Key West clocks are perpetually put to party time.
1. Modern Year’s Eve Red Shoe Drop
Photo: Andy Newman/Florida Keys News Bureau/HO
When: December
Ringing in the New Year is a drag — literally. Since , thousands of Key West onlookers verb gathered around Bourbon St. Pub to see local drag legend Sushi (aka Gary Marion) descend from the building’s second story in a six-foot ruby-red stiletto as the clock strikes midnight. The glittering spectacle is a campy take on NYC’s ball drop, and the eclectic crowds rival the hordes in Times Square. Adolescent families, leather daddies, and bohemian grannies all reveal up to cheer on Sushi and her gargantuan shoe.
An outdoor stage features other drag
FANTASTIC HEADDRESSES AND ENTERTAINMENT
42ND ANNUAL HEADDRESS BALL
Thursday, October 24,
PM
21 E. Quay Rd., Key West, FL
The Key West Business Guild is pleased to announce the 42nd annual Headdress Ball, an outrageous showcase of talent for mask-makers and costumers, will take place Thursday, Oct. 24, at Key West’s Coffee Butler Amphitheater in Truman Waterfront Park. Hosting this year will be internationally celebrated female impersonator, Randy Roberts. Showtime at PM. The Headdress Ball celebrates the creative and free spirit of Fantasy Fest, Key West’s day costuming and masking festival set for Oct. 17th – 26th., the Headdress Ball is Fantasy Fests premier LGBTQ+ event, hosted by the Key West Business Guild. Plans call for it to feature more than 15 contestants, all in awe-inspiring, unique headdresses, each hoping to walk away with the top prize. Although most participants are costumed from head to toe, entrants will be judged only from the shoulders up as they vie for the first-place prize of $3, Joining Randy Roberts and along with the headdress presentations
CLOTHING OPTIONAL DRESS UP!
BOWTIES & BIRTHDAY SUITS!
Wednesday, October 22,
PM
Fleming St.
Island House, “The Finest Gay Resort in the World" since , invites you to an EPIC, gay men’s clothing-optional pool party! All body types welcome and absolutely NO costumes needed! Mingle and frolic while rocking your bowtie alongside other like-minded guys in the pool, indoor & outdoor Jacuzzis, steam room & sauna! Great music, videos, friendly shot boys, and from PM enjoy HALF-PRICE DRINKS! 24hr food & bar! Admission includes Bowtie, lock & locker, pool towels, and resort access thru Thursday @ 4am. -Photo ID required. $50 cash/credit at the door. All gay, bi, trans, queer, + brothers welcome! -Party goes 5PM-8PM @ Fleming St.
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Don’t be fooled by its size: Tiny Key West knows how to pitch a big party, and the LGBTQ community puts on some of the best. From Carnival-style fêtes to gown-clown extravaganzas, the island’s panoply of queer festivals celebrates all members of the alphabet mafia throughout the year.
Plan your next Florida getaway around one of these eight events, when Key West clocks are perpetually put to party time.
1. Modern Year’s Eve Red Shoe Drop
Photo: Andy Newman/Florida Keys News Bureau/HO
When: December
Ringing in the New Year is a drag — literally. Since , thousands of Key West onlookers verb gathered around Bourbon St. Pub to see local drag legend Sushi (aka Gary Marion) descend from the building’s second story in a six-foot ruby-red stiletto as the clock strikes midnight. The glittering spectacle is a campy take on NYC’s ball drop, and the eclectic crowds rival the hordes in Times Square. Adolescent families, leather daddies, and bohemian grannies all reveal up to cheer on Sushi and her gargantuan shoe.
An outdoor stage features other drag
FANTASTIC HEADDRESSES AND ENTERTAINMENT
42ND ANNUAL HEADDRESS BALL
Thursday, October 24,
PM
21 E. Quay Rd., Key West, FL
The Key West Business Guild is pleased to announce the 42nd annual Headdress Ball, an outrageous showcase of talent for mask-makers and costumers, will take place Thursday, Oct. 24, at Key West’s Coffee Butler Amphitheater in Truman Waterfront Park. Hosting this year will be internationally celebrated female impersonator, Randy Roberts. Showtime at PM. The Headdress Ball celebrates the creative and free spirit of Fantasy Fest, Key West’s day costuming and masking festival set for Oct. 17th – 26th., the Headdress Ball is Fantasy Fests premier LGBTQ+ event, hosted by the Key West Business Guild. Plans call for it to feature more than 15 contestants, all in awe-inspiring, unique headdresses, each hoping to walk away with the top prize. Although most participants are costumed from head to toe, entrants will be judged only from the shoulders up as they vie for the first-place prize of $3, Joining Randy Roberts and along with the headdress presentations
CLOTHING OPTIONAL DRESS UP!
BOWTIES & BIRTHDAY SUITS!
Wednesday, October 22,
PM
Fleming St.
Island House, “The Finest Gay Resort in the World" since , invites you to an EPIC, gay men’s clothing-optional pool party! All body types welcome and absolutely NO costumes needed! Mingle and frolic while rocking your bowtie alongside other like-minded guys in the pool, indoor & outdoor Jacuzzis, steam room & sauna! Great music, videos, friendly shot boys, and from PM enjoy HALF-PRICE DRINKS! 24hr food & bar! Admission includes Bowtie, lock & locker, pool towels, and resort access thru Thursday @ 4am. -Photo ID required. $50 cash/credit at the door. All gay, bi, trans, queer, + brothers welcome! -Party goes 5PM-8PM @ Fleming St.
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