SPEND ENOUGH TIME IN KEY West and you get the sense that Fantasy Fest endures for far longer than one fun, party-filled week. Conch cottages island wide are still covered glitter, feathers, tulle and the rest of the detritus that comes with playing professional dress-up. And as we speak, piles of boas, stacks of tutus and corsets, and boxes of costumes are being hauled down from attics and dragged from under beds. Outfits (or lack-of-outfits) for every theme party are being meticulously plotted out to the tiniest accessory (or strategically placed scrap of clothing — one must avoid violating public decency laws, after all).
Yes, friends, the clouds of glitter in the air can only mean one thing: it’s almost time for Fantasy Fest here in Key West and the bodies — large, small, taut, squishy, old, young and many nearly naked — have already started arriving in droves.
Perhaps you’ve been stuck under a very large rock for the past few decades. If so, you’re forgiven for not knowing what Fantasy Fest is. Allow us to give you a brief Key West history lesson.
Back in 1979, Key West in October was deader than an iguana in winter. A small group of Key West locals, namely Bill Conkle, Tony Falcone, Joe Liszka and Frank Romano, figured a festival would be a genius way of boosting an otherwise dull and deserted time of year. This ten-day, (mostly) adults-only festival has since morphed into the largest event in the Keys, and one of the most unique and popular of its kind in the country. Imagine Halloween and Mardi Gras got busy one night in late January, and nine months later that beautiful union begat a screaming infant they called Fantasy Fest.
To hear locals tell it, the event started out small — quaint, if you’d believe such a thing — with early themes like “Old Key West” and “Va Va Voom.” Over time, it developed a decidedly more adult attitude (most participants of last year’s “Oh… The Games We Play” seemed to have been bused in from a board game convention where clothes are irrelevant, but Rich Uncle Pennybags spectacles ubiquitous).
It’s doubtful that founding member Joe Liszka could have foreseen today’s current iteration of Fantasy Fest. Liszka, who in ’79 was busy serving as the president of the Tourist Development Association of Monroe County, spent his days wracking his brain for strategies to attract more tourists to the Keys in the off-season. Always popular during the winter months amongst tourists fleeing the cold, business dropped significantly after the weather became more pleasant on the mainland. The snowbirds flew back to their nests, so to speak, leaving empty hotels and bars — and plummeting profits — behind them.
According to the official history of Fantasy Fest, Liszka lead fellow TDA board member Frank Romano down to Duval Street on Halloween and asked him to report what he saw. It turned out to be a trick question; Romano saw nothing, which was, Liszka explained, precisely the point. The island’s residents and shopkeepers had developed a distinctly European habit of boarding up their homes and businesses and leaving for vacation en masse during the scorching fall months of September and October.
To Liszka, there was no reason that Key West should conform to the typical tourist-driven template of high season/ low season occupancy. Key West was sunny and strange all year round — why shouldn’t its visitors take advantage of that fact all 365 days of the year? Liszka felt the island needed an injection of fun, something exciting that would draw crowds and reinvigorate the community during what had become a decidedly dreary time to be in the Keys.
Nearly 40 years later, Fantasy Fest — still celebrated during the ten days leading up to Halloween — has become the largest and most profitable of all of Key West’s events. Hotels, B&Bs and private rental homes sell out months in advance, with nightly rates skyrocketing in response. (During 2018’s board gamethemed Fantasy Fest, a single hotel room was reportedly rented for almost $700, twice its yearly average rate of $350.)
In the weeks leading up to October 1, costume stores spring up seemingly overnight, their aisles overflowing with feather boas, fishnet stockings, masks, makeup and wigs. But for some annual attendees, prep begins far more than a few weeks before the festival’s start. With many of the festival’s events offering thousands of dollars in cash prizes, seasoned attendees begin work on their costumes six to eight months in advance, or more, with results ranging from Broadway-worthy ensembles to skimpy outfits bordering on obscene.
Historically, Key West has been an oasis for some of our nation’s most dedicated drinkers. Indeed, during Prohibition, Florida remained the wettest state in the Union, maintaining its tourist-driven economy thanks to regular ocean shipments of “fish” curiously shaped like bottles of bootleg liquor. Throughout the 1960s and ‘70s, drugs were sold on Duval Street with the kind of fervor now relegated to $5 Spring Break T-shirt hawkers.
Though eventually the island was forced to clean up its act, there exists today a common misconception that, during Fantasy Fest, the usual laws are suspended in favor of an agreed upon ten-day no holds barred celebration that would make Hugh Hefner blush. The truth, however, is a bit less exciting: on Friday, Oct. 25, and Saturday, Oct. 26, a barrier is established around a few blocks of Duval and its adjoining streets, creating an official “Fantasy Zone,” inside the perimeter of which revelers may carry open (plastic) containers of alcohol. Backpacks, coolers, water guns and replica weapons are banned for obvious reasons, while mounted officers astride a herd of formidable, glossy-hocked police horses perform crowd control duties.
Technically, public nudity is illegal in Key West, but during Fantasy Fest that law in particular seems to stretch to about a millimeter before its breaking point, much to the delight of participants (and, sometimes, to the horror of a few wide-eyed families fresh off a Disney cruise ship whose travel agent neglected to mention their wholesome vacation would coincide with the raunchiest time of the year in the Keys). Body painting studios pop up along the length of Duval Street, with women ranging from nubile to decrepit lining up to have their torsos painted — which, the Key West Police urge people to remember, still does not actually constitute wearing a top. Therefore, the city requests that all bare breasts (painted to appear as the Hello Kitty logo or otherwise) remain inside the designated Fantasy Zone.
Before Fantasy Fest officially begins, you can build up your good karma for the week by attending the Womankind BraZaar Big Top Bash on Thursday, Oct. 17, at 7 p.m. at the Key West Theater (512 Eaton St.). Step right up to the greatest show on Earth and support Womankind during its signature decorated bra fundraiser, featuring a high energy live auction of sensational designs with a Big Top circus motif. The night will include a ringmaster of ceremonies, circus-style performances, games played by unsuspecting guests (it could be you!), spectacular surprises and “booby” prizes, a “rack” sale of artisan-crafted bras and a pre-auction welcome party with sweet treats and libations. Find out who’ll be “Breast in Show”; come as you are or break out your clown wig and make a deal on your favorite fabulous professionally created bra, knowing your partying is supporting preventative care for local ta-tas and Womankind’s mission of affordable healthcare for all. For more information, visit womankindkeywest.com.
This year’s Fantasy Fest — themed “In Tune but Off Key” — officially begins with one of the event’s only PGrated parties, the Goombay Festival. From noon to midnight Friday, Oct. 18, and Saturday, Oct. 19, Goombay sees the historic neighborhood of Bahama Village turned into a kind of folksy, exuberant block party, complete with food and craft stalls, though the heart of the festival is undoubtedly the nonstop musical performances. Featuring a wide range of acts including reggae, funk and gospel, the stage at the intersection of Petronia and Fort streets becomes an inclusive dance party for the island’s residents and tourists just beginning their Fantasy Fest vacation. It’s a joyful two days, accented by the delicious smell of street meat and the promise of all the frozen drinks in hollowed-out fruit your little lush heart could ever desire.
It can get hot out there in Bahama Village, so we recommend you hit the pool — the Havana Cabana Pool Party presented by Beso Del Sol Sangria, to be exact. Cool off in the largest pool in Key West while DJ Top Jimmy spins the hottest beats and the on-site Floridita food truck serves up authentic Cuban specials. The party runs from 1-5 p.m. and admission is free, so you have extra mojito money.
Of course, no Fantasy Fest is complete without its special brand of monarchy. For those unfamiliar with the symbolic coronation of the King and Queen of Fantasy Fest, you’re in luck: everyone is welcome to attend the official Royal Coronation at the Truman Waterfront Amphitheater from 6-9:30 p.m. on Friday, Oct. 18. In true Key West fashion, the election of this year’s monarchy is less pomp and circumstance, more flamboyant fabulousness, with a three-course plated dinner, a two-hour stage show and appearances by local celebrities. Once crowned, the King and Queen (awarded for having raised the most money for A.H. of Monroe County during their two-month campaigns) will preside over the rest of the week’s parties, parades, galas and fetes.
Sunday’s ever-popular (and very family friendly) Zombie Bike ride is certainly not to be missed. What started as a rag-tag bunch of weirdos careening down South Roosevelt in zombie makeup has evolved into a traffic-stopping, nation news-covered theme ride from East Martello to downtown Duval Street. Though the event has become less of a “ride” than a start-and-stop, slow-moving parade of fantastically zombified riders trying not to crash into one another, bike traffic along the four-mile route usually decongests enough towards the end of the highway to allow for a friendly breeze or two.
There are no limits or expectations for costumes. Some riders look ready for their next scene on The Walking Dead, while others might smear some fake blood on their shirt and call it a day, but the more effort you put into your costume, the better, since families camp out in chairs along the way, cheering and filming. It’s a unique spectacle, to be sure, so tell friends out of town to keep an eye out — you might just make the evening news.
Monday evening starts out with a bang — of a starter’s gun, that is — when the annual Heroes and Villains Run/Walk 5K takes off from the Southernmost Beach Café (1405 Duval St.) at 6:30 p.m. Dress up as your favorite hero or villain, make your way to the finish line as fast as you can, and you’ll be in the running (pun intended) for prizes like “funniest costume,” “most creative,” and more. The run ends, as all runs should, with a sunset beach party, after which the beach transforms into a BBQ. Register for the race at www.themeruns.com.
On the other side of the spectrum, the unofficial but always titillating Kinky Carnival at First Flight Island Restaurant & Brewery (301 Whitehead St.) kicks off at p.m. on Monday night, with costumes required for entry — and make no mistake, these are some serious fetishists. The longstanding tradition has resulted in Monday night’s becoming an informal Fetish Night island-wide. Keep an eye out for pop-up BDSM parties (how many times have you heard that one at home?) and enjoy wandering around the Fantasy Zone for your first glimpse at just how far some people try to push the boundaries of “I swear, officer, I’m not naked.”
If you want to celebrate the Free Love movement without the actual love part of it, you should find yourself at the Green Parrot for the increasingly cultstatus Beatles Band. Past Beatles tribute shows have had their rabid fans swinging from the rafters as they danced, laughed and sang along to a set-list pulled from decades of Lennon and McCartney hits. Come dressed as your favorite Beatles lookalike or dress in theme and help turn the Parrot into the 1967 Summer of Love. Shows at 5:30, 9 and 11 p.m.
Oct. 22 offers up a whole range of festivities, including an animal-themed all-you-can-drink SPCA party at the Rick’s Complex (202 Duval St.), a Beach Bash featuring Patrick and the Swazyees at the Southernmost Beach Café and of course, the always epic Captain Tony’s (428 Greene St.) Party in Plaid, aka the perfect excuse for having held onto those horrifying madras pants for all these years. For a more obvious thrill, there’s also the Men of Labare Tighty Whitey Party at BottleCap (1128 Simonton St.), featuring the all-male Adonislike revue made famous by the Magic Mike movies. Dress code encourages sexy white underwear (not an oxymoron, contrary to what Cosmopolitan and GQ have to say) and tickets are limited. If it was good enough for national treasure Channing Tatum, it’s more than good enough for Key West.
One of this author’s favorite Fantasy Fest events is Tutu Tuesday, a multi-stop, multi-venue, roving spectacle of tulle and fluff. Local bar entrepreneur Chris Shultz and his best bud DJ Jevne Miller created the Tutu Party 11 years ago, and over the last decade this party has become one of the most outrageous and well-attended events of Fantasy Fest. This year’s magic-themed Tutu Party is shaping up to be the most original and best party yet.
The tutu shenanigans start at 5:30 p.m. with a pre-party at the technicolor 22&Co. (504 Angela St.). Pick up a wristband, enjoy a glittery cocktail and then hustle down to Mary Ellen’s (420 Appelrouth Lane) so you can join the tutu-wearing hordes. Parade through downtown, stopping at First Flight, Tiki House and Rick’s, before the party starts at General Horseplay (423 Caroline St.).
The infamous Tutu Party DJs (16 of them, in fact) will be offering up something for everyone in the various rooms of the party complex, and this year they are featuring live music in the courtyard and live acrobatic performers on the Teasers stages. There have been over 2,000 people at this event the past three years, and somehow they have found a way to make room for more! So fish out that tutu and put on your dancing shoes — this is a party you don’t want to miss.
Wednesday through Saturday are when Fantasy Fest really gets going, with multiple themed parties — some official, some unsanctioned — happening throughout downtown. Some of the legendary ones: Wednesday’s Pet Masquerade, where a procession of costumed pets and their incredibly crafty owners make their way across a stage at the Truman Waterfront Amphitheater to compete for prizes; Wharfstock, where prototypical pirate hangout Schooner Warf transforms itself into a psychedelic love-child groove fest, complete with body painting contest; the 37th annual Headdress Ball on Thursday, where the phrase “the closer the headdress, the closer to God” gets tested out for serious cash prizes; an all-day, all-night street fair with crafts, food and last-minute souvenirs; the 19th annual Living Art Expo, where the best “human canvases” are awarded thousands of dollars; a White Party, Red Party, Blue Party, Pink Party, Toga Party, Slumber Party, Kinky Couple’s Party, Glow Party, Pirate Party, Foam Party and Pajama Party; and, of course, the Dungeon of Dark Secrets party, which is exactly what it sounds like.
There are also two massive parades: the first, the locals-favorite Masquerade March, happening Oct. 25, for which thousands of costumed pedestrians gather to parade themselves through downtown to the delight of onlookers handing out shots and beads. And then, there’s Saturday’s pièce de résistance: The Official Fantasy Fest Parade, a confetti-throwing, band-booming, float-filled colorful masterpiece to end the festival on a very, very loud note.
Perhaps unsurprisingly, your entertainment options for the week are also on the sultry side. From Oct. 23-25, Key West Burlesque presents “The White Rabbit’s Wonderland: A Burlesque Parody” at the Key West Theater, where you can take a trip down the rabbit hole to a world where the March Hare dances with a bare derriere and tea parties are way more tasty when the Mad Hatter is only wearing pasties. “The White Rabbit’s Wonderland” follows the perennially late fluffy bunny on his journey around a risqué wonderland filled with bodacious versions of all of your favorite Carroll-esque creatures. The show runs for three nights only at the intimate Key West Theater, and after the success of last year’s “Madame DuJour’s Magical Game Show and Burlesque Experience,” it’s sure to sell out fast. Tickets are available at www.thekeywesttheater.com.
If you’re still alive by Sunday, congratulations! May we suggest scraping yourself off the floor and attending the annual “Fat Lady Sings” Tea Dance at La Te Da (1125 Duval St.)? We have it on very good authority that yes, there will be a fat lady present, yes, she will sing, and that afterwards, all of it, finally, will be over.
At least, until we learn the theme for next year.
The full list of events, including tickets, start times, and contact info for all official Fantasy Fest events (yes, even the naughty ones) can be found at www.fantasyfest.com. ¦