Every culture worth its salt has a few days when the rules come off.
Carnival in Rio.
Mardi Gras in New Orleans.
The masked balls of Venice where for a while the fishmonger and the duke couldn’t tell each other apart and nobody was supposed to try.
Key West, which frankly never had many rules to begin with, didn’t get its own until 1979, when October on the island was a sleepy, sweaty, mostly empty stretch and somebody looked at all that quiet and said “costumes, everybody, now.”
The island said yes the way it always says yes, too loud and without shoes, and forty-some years on it’s ten days of parades and masquerades and theme parties and somebody’s uncle in a feather boa he swears he’s giving back.
Here’s how it got like this. Get a glass of water first, and maybe a real drink after.
A party for the slow season
It started the way a lot of good things start in small towns, with a handful of shop owners and a bad month.
Tony Falcone and Bill Conkle ran Fast Buck Freddie’s on Duval, Frank Romano and Joe Liszka ran Key West Aloe, and every late October the summer crowd went home and the winter crowd hadn’t shown up yet and the whole town just sat there blinking in the heat like a lizard on a porch, waiting for somebody, anybody, to buy something.
Every place that lives on visitors knows that feeling, and most of them answer it with a food festival or a sidewalk sale, which is how you know Key West is not most places, because Conkle’s answer was Halloween, since everybody here already loved dressing up anyway, and that might be the most Key West sentence anyone has ever said out loud.
Falcone, for his part, has said the reason was partly psychological. “This is when all divorces would happen,” he told WLRN in 2019, which tells you a great deal about island life in the off-season and also that you should probably not ask a follow-up question.
The night it all started
The first one kicked off on Friday evening, October 26, 1979, when a character called the Mistress of Madness turned up at Mallory Square, the same waterfront where people were already gathering to applaud the sunset like it had done something clever, so the bar for spectacle on this island was never low.
That night there was a masked ball at the Casa Marina, and the next evening the Grand Parade rolled, and this is where the history goes a little soft around the edges, the way history does when everyone involved was having a very good time.
Robert Kerstein, who wrote a whole book about this town called Key West on the Edge, counts about seventeen floats, and Falcone remembers around 22, so pick a number, nobody’s going to fight you on it. Everybody agrees on the headliner though, a local personality painted head to toe and riding the front of a big car as its hood ornament, which is not a sentence you find in the history of many parades.
Nobody was getting rich. For the first couple of years the organizers kicked in their own money to cover the bills, and after that first parade the founders were out on Duval Street with brooms, sweeping up after their own party, which is a level of personal responsibility this town has rarely seen before or since.
Themes, crowns and a lot of money for good causes
Every year has a theme, and the whole island builds its costumes and floats around it with the devotion of a village getting ready for its saint’s day, only with more glitter and worse decisions. In 1983 it was “The Plays of Tennessee Williams,” the island’s second-most-famous writer depending on who you ask at Sloppy Joe’s, who had died that February. 2019 was “In Tune But Off Key,” 2024 was “It’s a 90s Neon Cosmic Carnival!”, exclamation point theirs, and this year it’s “Musical Icons and Iconic Musicals,” so expect a lot of people who are very sure they look like Freddie Mercury.
Then there’s the royalty. Since 1989 the King and Queen of Fantasy Fest haven’t been born or elected so much as funded: candidates campaign by raising money, and the winners get crowned at the Royal Coronation that opens the festival. For more than 30 years that money went to AH of Monroe County, the group that started out as AIDS Help, and that’s worth sitting with for a second, because through the years when a lot of the country was looking away, this party town was raising money in sequins. By 2022, 64 royal pairs had been crowned and more than $5 million raised. Since 2023 it all goes to the Florida Keys SPCA, so the crowns are for the dogs now, in the best possible way.
From one weekend to ten days
What started as a weekend is ten days now, and like any old festival anywhere it has grown its own little rituals, the way a boat that never leaves the harbor grows barnacles:
- Goombay, the street festival in Bahama Village celebrating the island’s Bahamian culture, which has kicked things off for more than 30 years and is where you go to eat something off a grill and remember how much of this town came over from the Bahamas.
- Tutu Tuesday, which is exactly what it sounds like, on every body type, at every age, with zero apologies.
- The Masquerade March through Old Town, free to join or just watch and sometimes called the locals’ parade, which is about as close as Fantasy Fest gets to a secret handshake.
- Sloppy Joe’s Toga Party, on its 47th go-round this year, and the Key West Headdress Ball, on its 42nd, both of which have outlasted most marriages, possibly for related reasons.
- The Fantasy Fest Parade on the last Saturday, still the main event, expected in recent years to pull more than 60,000 people onto a street that runs from the Gulf to the Atlantic, which on this island is not nearly as far as it sounds.
Hurricanes, a pandemic and a very long reign
It hasn’t always gone to plan, because nothing down here does. In 2005 Hurricane Wilma came through and pushed the whole festival into December, which is a very Key West way of saying the party was rescheduled, not cancelled. In 2020 COVID actually did cancel it, with the festival’s director calling it “the most responsible decision we can make,” a phrase that may never before have been spoken in connection with Fantasy Fest. And because of the pandemic, the King and Queen crowned in 2019 held their titles for three years, which in island time is basically a dynasty.
Fantasy Fest 2026
This year it runs October 16 through 25. The Fantasy Fest Parade rolls on Saturday, October 24, and the whole thing ends on Sunday the 25th with “The Fat Lady Sings” Tea Dance, which is either the best name for a closing party ever invented or a warning, and either way it’s honest. Everything still to come, the parties and the parades and the shows, with times and how to get in, is on our Fantasy Fest 2026 page. Go. Wear something. Wear sunscreen under it.
Sources
- WLRN: Key West’s Fantasy Fest turns 40, a founder looks back (2019)
- Robert Kerstein on the first Fantasy Fest (guest post, 2012)
- WLRN: Fantasy Fest begins with King & Queen coronation (2018)
- Keys Weekly: Key West crowns Fantasy Fest King & Queen (2022)
- Florida Keys & Key West: Masquerade March (2024)
- Florida Keys & Key West: Goombay (2019)
- Keys Weekly: Hurricane Wilma and Fantasy Fest
- NBC Miami: Fantasy Fest cancelled for 2020
- Key West Chamber of Commerce: Fantasy Fest 2026
