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10 Things to Know about Fantasy Fest in Key West, Florida

Thinking of going to Fantasy Fest in Key West? Here are 10 things to know before you go.

By Brooke Morton

January 6, 2014

Fantasy Fest in Key West, Florida, gives us Halloween on steroids, but it’s more than that. Especially for women, it’s a relatively safe, encouraging environment to be on display for those who so choose. Those who bare receive overwhelmingly positive feedback. Think about it: It’s rare that women — and men, too — can be so free without a freight train of consequences. Here, it’s safety in numbers because, for better or for worse, nearly everyone is doing it.

What You Don't About Fantasy Fest | Key West Fantasy Fest | Florida Keys Events | Duval Street

It’s as innocent — or as dirty — as you want it to be.

Fantasy Fest is a Rorschach test of sexuality: You see what you want to see. I lean toward naivety, so at first, I saw only happy people seeking freedom from the burden of clothing. It was also 4 p.m. As time danced later into the night, the more I saw that Duval Street was like a bar at closing hour, but largely absent of the indifferent. I also suddenly realized that the whips, handcuffs and the like were more than just costume props. Credit

What You Don't About Fantasy Fest | Key West Fantasy Fest | Florida Keys Events | Big Nude Boat Cruise

Don’t be confused: Fantasy Fest welcomes all, but your average attendee isn’t a tree-hugging naturist.

Last February, I joined Bare Necessities’ Big Nude Boat cruise, cobbling together a portrait of nudists as innocent, typically monogamous couples who simply like sun on their backsides. Naked, we swam in rivers, hiked along trails and frolicked on beaches. I thought nature was part of the deal. No so with Fantasy Fest. For starters, most of the events were at night and held in bars. That should have been my first clue. Credit

Inhibition is masked — literally.

Nudists — naturists especially — want to be seen for who they really are, mastectomy scars and all. Costume parties are part of that scene, but not the defining factor (picture how odd someone would appear if nude at the beach save for a mask). Now consider Fantasy Fest. Even the name tells us this is a celebration of what isn’t real. It’s about costumes and masks, which give us permission to hide, to be someone else — even if that is simply a more daring someone. Add in the effects of crowd psychology and it’s easy to see how easily and quickly things turn wild. Credit

You’re not fully undressed without a smile.

One thing that Fantasy Fest and the Big Nude Cruise have in common: Naked people are friendly. In Key West, even on the nights when I was wearing not a costume but everyday clothes, people chatted me up. And I don’t mean men with an agenda. Ladies asked me if I was having fun and if I’d help them choose between airbrush paint designs. These folks might not peer-pressure you out of your clothes, but certainly from your shell of shyness. Credit

People like to get away with stuff.

Fantasy Fest is about being naughty on lots of levels. One night as I stepped into the elevator at Casa Marina, a Waldorf Astoria Resort, a gentleman called out to me to hold the door. He was drinking a Peroni beer, and packing two more in the generous pockets of his cargo shorts. He was giddy when he asked, “You don’t see these, right?” I had to laugh. For most of the year, Key West doesn’t allow open containers. During Fantasy Fest, they mark off a “fantasy zone” several blocks long where open containers are allowed. From what I saw, the cops didn’t want to be buzz-kills; rather, they stepped in only if folks became a public nuisance. Credit

Exhibitionism is her idea. (He might like to get nude, but she likes to show-off.)

On the nude cruise, I met couples that expressed that the trip — and the nude lifestyle — was his idea. That didn’t surprise me. In Key West, I met about a dozen couples that all expressed that Fantasy Fest and body painting had been her idea. This did. Credit

A thong does not a pocket make.

If you’re a man charging ahead into the great pant-less unknown, think twice about where you’re going to tuck your valuables. Bill Hoebee, a radio host in Key West, says that bartenders refuse money pulled from thongs. Even if they don’t see the removal, they’re not happy if handed bills from a thong-clad chap who doesn’t seem to have anywhere else to stash his cash. Hoebee assures me that bills pulled from between boobs are always considered good currency. Credit

Show Duval Street, show the world.

Nothing about Fantasy Fest is private, save for your own bits if you choose to keep them that way. If one boob-hungry paparazzo asks a baring-all soul for a snap, suddenly it sounds like a plague of locusts as dozens of passersby click their lens caps from position and iPhones buzz to life. Credit

And yet, here paparazzi are told “thank you.”

Fantasy Fest is about something greater than thrills. I talked to 20 or so women who willingly posed topless for anonymous cameras. A few were shy about having their pictures taken, but they were the minority. Others did all but leap in front of the lens. Older and less fit women often thanked those who stopped the folks who stopped to ask for a photo. Nearly a dozen fit women in their 20s and 30s told me that the attention validates them and all the effort they put into looking good. They feel happy because, for a few days, they know what’s like to be famous, or at least a camera darling. Credit

Watch is also a verb.

You may be surrounded by folks ready to dress up, dress down, cross dress or whatever — but this is not likely their first rodeo. Most revelers I chatted up had Fested anywhere from one to 29 times before. Remember that it’s more than OK to just watch. After all, the world would have no exhibitionists if there was nobody to simply look on. Credit