IF YOU’RE READING THIS WITHOUT a crushing headache, color us impressed. You’ve made it through the first half of Fantasy Fest. Most likely, you’re a little bruised, a little battered and more than a little hungover from a week of late night partying fueled by Five Hour Energy and shots of Fireball.
So far, you’ve zombified yourself and ridden your bike perilously down South Roosevelt, you’ve donned your tutu for the Magic Tutu Party and you may have even tied a cape around your neck and run a 5K (in which case you are truly a superhero and I salute you and your physical fitness). If you’ve gotten to this point relatively unscathed, chances are you’ve been pacing yourself because you know that the best is yet to come.
The wise among you have already combed through your extensive costume collection and supplemented it accordingly for this year’s People’s Parade (to clarify: that’s the local’s name for Friday night’s walking parade. Technically, the People’s Parade, or Locals’ Parade, is called the Masquerade March; feel free to use the latter if alliteration turns you on).
Sloppy Joe’s annual toga party is a sure bet for Thursday night festivities. COURTESY PHOTO
It’s true that many out-of-town Fantasy Fest enthusiasts start prepping their outfits months in advance, while the festival’s most dedicated attendees start getting targeted Search Engine Optimization ads for corsets and rainbow wigs as early as March. But for many locals, there’s a mad dash to the Halloween store or a frantic text sent to a few friends in the hours leading up to the annual Friday night parade, when everyone you know, their brother, their brother’s ex-girlfriend, their brother’s ex-girlfriend’s aunt and a gaggle of Montessori moms dressed like sexy Wizard of Oz characters (and yes, sexy flying monkeys are among them) crawl toward Duval Street. Yes, living in Key West might be stressful at times, but getting a text that says, “SOS – CAN I BORROW YOUR FREDDIE MERCURY MUSTACHE AND GOLD LAMÈ ONESIE?” on Friday afternoon lends a certain kind of levity to the most dragging of work days.
Make sure to secure a spot on Duval Street to watch Saturday night’s parade down Key West’s main drag. COURTESY PHOTOS
Whether you’ve arrived bearing luggage leaden down with spandex unitards and platform boots, or you’re googling “last minute Fantasy Fest costume” (which, by the way, is really, really NSFW), the truth is that you don’t need much to have fun at this year’s festival … just an open mind, a fortified liver and a tolerance for weird and wonderful sights.
For those crazy dreamers who began Fantasy Fest in 1979 as a way to stimulate the flailing tourism economy that plagued Key West in October, getting even a few extra hotel beds booked would have meant their project was a success. Surely, no one could have imagined that the event would grow to become the most profitable and infamous event of the year. In a town that likes to think it had already cornered the market on abnormality long before 1979, seeing someone’s dear grandmother strut down Duval Street wearing not much more than a pair of precariously placed pasties has really put our little ten-day festival on the “Bucket List Experience” map.
Dress up your furry friend and hit the Pet Masquerade on Wednesday.
This year, attendance is estimated to approximate 100,000 costumed bodies. And while those ten days certainly don’t start out slow (there are about five parties a day starting Oct. 18), the festival really finds its groove around Wednesday, Oct. 23, with the Rock and Roll Revitalizing
1960s Pool Party, presented by Blue Chair Bay Rum and hosted by the Marker Resort (200 William St.). Give in to nostalgia for a time when The Beatles were scandalous (and keep that in mind while you’re surveying the crowd to see how far we’ve come in our definition of shocking behavior) while floating in one of the Marker’s pristine palm-lined swimming pools.
The boogie starts at 1 p.m., which, if you’ve done Tutu Tuesday right, should be just about when you wake up. After you’ve had your fill of Pink Squirrels and danced your hangover off to the rocking tunes of local celebrity band Patrick and the Swayzees, make your way over to the Key West Amphitheater at the Truman Waterfront Park (21 E. Quay Road) to watch the Pet Masquerade, one of only a few family-friendly events, and certainly the only party where the pets will be wearing more clothing than the humans back on Duval Street. It’s a goofy, light-hearted event that never fails to entertain, after which your evening plans get complicated.
Fantasy Fest offers many parties and opportunities to indulge your costuming creativity.
Do you slip back in time to the ’60s at Schooner Wharf Bar’s Wharfstock (202 William St.), where your peace beads and tie-dye will be totally groovy, man? Or do you go sip under-the-sea-themed Shark Attacks at the Blue Party, hosted by Lucy’s Retired Surfer’s Bar (221 Duval St.)? Or perhaps you’re craving something with a little more color, in which case the eighth annual Luv2Glow Party at Mary Ellen’s Bar (420 Appelrouth Lane) is sure to satisfy your need for a black-lit place to get freaky on the dance floor amidst a set of sexy, neon-hued glo-go dancers. (If you’re not sure about all that glow paint, keep in mind that black lights make your teeth look really white.) For color of a different hue, hit Fogarty’s (227 Duval St.) infamous Red Party, where DJ Jimmy Jamz will keep you dancing all night long.
The later the hour, the closer you get to the adult-themed parties that have made Fantasy Fest famous. There are two parties on Wednesday that give a whole new meaning to the phrase “Venerean mirth”: the ABC party at Sandbar Sports Grill (511 Greene St.), featuring Hooters Super Model Jessie Teschker and a dress code that prohibits clothes but accepts anything else. And you don’t need us to tell you that, if you’re trying to decide whether to take your kids to this or the Pet Masquerade, you should probably choose the latter.
You can also try your luck in the Dungeon of Dark Secrets, which formally requests that you embrace your fantasies while wearing your choice of risqué, non-breathable fabrics (a mystery to those of us who sweat at the mere mention of humidity): leather, latex, PVC, Levis, etc. Legendary drag bar 801 Bourbon (801 Duval St.) is hosting the evening, so expect to see the cutest go-go dancers on the island in their tightest tip-encouraging skivvies (not that kind of tip, get your mind out of the gutter).
If you’ve made it to Thursday, pat yourself on the back and check in with the little angel and devil perched on your shoulders — they’ll advise you on what to wear to the Dante’s Halos & Horns Pool Party at Dante’s Restaurant & Raw Bar (951 Caroline St.). Beginning at noon, the party promises free body painting, live music, giveaways, food and drink specials, and a special elevated stage in the middle of the pool (let that sink in) for showing off your best hungover dance moves. Now in its 13th year, this event is totally wild and will leave you soaking wet (it’s a pool party, so bring your bathing suit and leave your shame at home). Oh, there’s also pole dancing contest, because why the hell not?
Later that evening, you’d be lucky to score entrance to one of the earliest events to sell out each year: the 37th annual Headdress Ball presented by Stoli Vodka. Hosted by the Key West Business Guild (the first gay-centered guild in the nation) the event is heralded as the premiere gay and lesbian party of the year. With a $3,000 cash prize, the costumes for this party are definitely not of the last-minute kind; this is a professional-level, show-stopping competition that begins and ends with a dance party, with lines around the block of hopeful lookieloos desperate to catch a glimpse of one of the winner’s towering creations. And the venue, the Key West Amphitheater at the Truman Waterfront, allows early arrivers to enjoy the nearby street vendors and haunted floating veteran’s museum, the USCGC Ingham.
If you find yourself without a ticket to the headdress ball, don’t freak out — just borrow a sheet from your hotel room and practice your best Belushi (the Animal House chanting part, not the speedball overdose part) as you attend Sloppy Joe’s 40th annual Toga Party (201 Duval St.). Gift card giveaways to the best toga begin at 8 p.m., with proceeds to benefit local charity A.H. of Monroe County.
Choose a classic all-white sheet if you want to knock out two parties with one set of linens, since Rick’s fourth annual White Party (202 Duval St.) is just across the street. DJs spread throughout the complex’s eight bars will be spinning a variety of musical styles all night. Expect live music from the DurtBags, exotic dancers and a “color splatter room” lit with black lights — think Jackson Pollock meets bachelor party.
Do-gooders with a thirst for competition as well as booze should put on their best pink clothing or body paint and try their luck at $850 worth of bar tab prizes at the Fat Tuesday Pink Party (305 Duval St.), where a portion of the evening’s proceeds will go to the American Cancer Society – Making Strides Against Breast Cancer of the Florida Keys.
Traditionalists may prefer to compete for the $700 Hugh Hefner and Marilyn Monroe look-alike contest at the Pajama and Lingerie Party at The Dirty Pig (320 Grinnell St.), where if you close your eyes (and throw back enough booze) you might think you’re partying at the mansion. Or you can trade the Playboy Mansion for Wonderland at The White Rabbit’s Wonderland: A Burlesque Parody at the Key West Theater (512 Eaton St.), where you’ll follow the White Rabbit of “Alice in Wonderland” fame around the risqué world of burlesque wonderland.
It might be the most naughty party of the whole week (and that is saying a lot), but the Exposed Party hosted by Bourbon St. Pub’s Adult Entertainment Complex (724 Duval St.) is worth a trip, if only for the people watching. A true Bare What You Dare dress code means full nudity throughout, plus activities like naked swimming, naked hot-tubbing, naked foam pit-frolicking, exotic dancers and a truly impressive spectrum of pornography. And glow sticks! It’s the little things, kids.
Friday means the aforementioned Masquerade March/People’s Parade/ Locals’ Parade, but also the complete surrender of Duval Street to crowds of half-clothed exhibitionists brave enough to venture out in the daylight to enjoy the mile-long street fair and dance party that starts at noon. The afternoon is a fairly quiet one,unless you have a Y chromosome, which will gain you entry into the exclusive Bowties & Birthday Suits party at the Island House (1129 Fleming St.). This dudes-only dance party boasts a 24-hour clothing optional poolside bar and café. The doors open at noon, and will be guarded by bouncers who aren’t kidding when they say, “No Girls Allowed.”
The rest of you will have plenty of time to line up at the Frances Street cemetery entrance by 5 p.m. for the walking parade, after which your options for evening attire get weird. If you look good in a ruffled shirt and can work a mean eye patch, go out for the $1,500 in cash prizes at Turtle Kraals’ 13th annual Pirate Bash (231 Margaret St.). The doors open at 7 p.m. and there’s plenty of booty for the plundering, if you’re into that sort of thing. If you look good standing next to Ron Jeremy (let’s be honest, who doesn’t at this point?), the Pimpin’ Ain’t Easy party at Cowboy Bill’s (618 Duval St.) is your only chance to meet the man himself.
Those with an affinity for glitter and glow-in-the-dark paint will love the Glitter and Glow Party at Sidebar (504 Angela St.) — the theme is self-explanatory, so let your artsy-craftsy side go wild.
If you look best in nothing at all, first: congratulations, and second: get thee to the 19th annual Living Art Expo presented by Brown Sugar Bourbon at Sunset Pier (0 Duval St.), where beautiful human bodies serve as canvases for artists vying for $3,000 in cash and prizes. Into watching sexy ladies (and dudes who look like sexy ladies) do sexy things? You’ll want to play games with Lady Lethe at the Kinky Couples Party at 801 Bourbon Bar, where the Lady herself will stun you with her titillating, jaw-dropping performances. The show starts at 8 p.m. and tickets can (and should) be purchased ahead of time.
Saturday means resting up for the evening’s parade, but you can venture out early and enjoy the nonstop party on Duval Street if you have the energy. Then, at 7 p.m., join about 60,000 paradewatchers at this year’s official In Tune But Off Key Bud Light Fantasy Fest Parade. Stake out your spot early or risk standing in back of someone wearing too few articles of clothing to be standing so close. Floats of all sizes and budgets will crawl slowly down Duval Street, accompanied by street dancers, marching bands and coordinated troupes of all kinds who will happily pelt you with beads.
Stay alert, or get up high by booking a ticket to one of the many private balcony parties on www.keystix.com. After the parade (if you’re still standing) you’ve got a chance to attend the last risqué parties of the week: the Dirty Doctors and Naughty Nurses Party at the Key West Theater and the Surfers and Sirens Party at the Breakfast Club, Too (610 Greene St.). Then GO TO BED because you have to be up in time for the Fat Lady Sings Tea Dance at La Te Da (1125 Duval St.), which begins at 4 p.m. on Sunday and serves as the last official event of Fantasy Fest 2019.
Sunday also happens to be Children’s Day (and yes, this is an actual children’s day, so put on some clothes for heaven’s sake or risk jail time) with arts and crafts, rides, games and snacks happening at Bayview Park from noon until 5 p.m. The event’s only adult entertainment consists of standing alongside local sleep-deprived parents rubbing the last remnants of glitter out of their hair and wondering how they’re going to get through next week without falling asleep in public.
Or, if you’re headed home, remember: there’s a fully stocked bar in the departures lounge of the Key West International Airport. And yes, the airport still counts as Fantasy Fest territory, meaning it’s totally acceptable to down a couple rum runners before your 11 a.m. flight back to Montana, or whatever snow-covered, landlocked landscape you flew in from. As for those of us who are insane enough to call this island home, we’ll be spending Sunday in full recovery mode, tucking away stacks of tutus and slightly worse-for-wear wigs, and swearing in unison that next year, we’re only going to one or two events — hand on glow paint-covered heart. ¦