Key West’s wildly popular festival celebrates its 40th year of creative masterpieces and whimsical debauchery. This year’s theme, “In Tune But Off Key,” ushers in a season full of musical jaunts and genre-bending displays. Here is your guide to the second half of this costumed extravaganza.
Masquerade March
Oldtown
Oct 25th | 5.30PM
It’s a bird! It’s a plane! No. It’s actually your bicurious neighborhood doctor in platform heels and an Elton John Rocketman get up. The locals take over for this feet first, automobile free version of Saturday’s theatrical displays. Come make your way through the historical sites of Key West starting at Oldtown Cemetery on this costume-fueled self-guided walking tour you never could quite imagine back in the Midwest or wherever you fled. Colloquially known as the Locals Parade, it carries all the pomp and costuming of the following day’s debauchery, just on foot. Grab free drinks and unsolicited advice along the way from cheering residents and businesses that are kind enough to quench your thirst but not so kind as to allow you bathroom privileges. It’s delicious mayhem that shows the island’s creativity at its finest. Naturally, there’s a super secret infamous pre-party happening somewhere in the vicinity. Best of luck finding it!
What to look for: Egyptian gods on stilts and pimped out tricycles with surround sound boom boxes. They signal the funnest groups and the fastest ways to cut through the crowds.
The Bud Light Fantasy Fest Parade
Whitehead St & Duval St
Oct. 26th | 7PM
Crowds stretch from the Gulf to the Atlantic in a frenzied bid to catch beads that cost 1/1000th the price of your VIP seating. It’s the shorter version of Mardi Gras! The 40th anniversary’s theme “In Tune But Off Key” will empty Amazon warehouses across the country of shiny disco wear and mauve synthetic wigs. If you’re lucky enough to know someone who knows someone who owns a house big enough to park a flatbed, getting onto a spectacular float can be a once-in-a-lifetime opportunity. Not keen on roving the street in front of news reporters? Stay above the masses with all-inclusive balcony and patio parties across the strip at restaurants and bars ready to gouge last-minute purchasers. We recommend grabbing a view closer to Front Street, long before intoxicated revelers become exasperated. Since it all concludes within an hour or so, you won’t be held captive too long on this marquee night of the festival.
What to look for: That one guy who thinks this is the best time to propose to his partner. Entries by WeBeFit and the Mystick Krewe of Key West.
The Rocky Horror Show
310 Wall St | Waterfront Playhouse
Oct. 19th – 25th
Why not? You’ve seen it just about everywhere else. Come view the theatrical version put on by one of the weirdest cities in the continental US. The sharp-tongued and delightfully wicked local performer Christopher Peterson leads the key weird crew of misfits for this intimate and bizarre retelling. No word yet on whether a motorcycle will barrel through the audience, but on this island of misfit toys, you can expect some hilarious spins on this iconic tale.
What to look for: All the locals you won’t run into for another year.
Surfers and Sirens Party
610 Greene St | Breakfast Club, Too
Oct 25th | 8PM
One of the newest restaurants and the recently debuted Key West Mermaid Festival team up to present their first annual post-parade shindig. The ecstasy of the Bud Light Fantasy Fest Parade can disorient even the most seasoned revelers. The addition of this Surfers and Sirens ball keeps the momentum going at a time when scattered partiers may want to wind down. Given its infancy we’re not quite sure what to expect, but mermaid aficionado Kristi Mills has a knack for setting the bar high. We’re curious to see how one maneuvers thirty pound of prosthetic tails on the dancefloor.
What to look for: That one soul who comes dressed as Ursula not knowing the 1989 version was based off of infamous drag queen Divine. That puts you on the rainbow spectrum, darling.
Fat Lady Sings Tea Dance
1125 Duval | La Te Da
Oct 27th | 4PM
The last official event of Fantasy Fest 2019! This is your final – and possibly best – shot to reach out and connect with that cute queer before they return to whatever frozen tundra they call home. This is an all-inclusive dance fest with historical ties to the LGBTQ+ community. While you may not hear to latest remix of Lizzo, you will undoubtedly get to relive such illustrious divas as Donna Summer, Madonna, Tina Turner, and Cher. Above all, a tea dance is a feel good celebration with a nod to less turbulent times.
What to look for: Bourgeois queens who think mother’s pearls elevate them above the peasants. Your future partner!
