13 Inevitable Stages of Fantasy Fest, Halloween, The Florida Keys (Photos)

Alas, the 13 Fantasy Fest phases:

1. Preparing your costumes.

Thou does not simply wear a cocktail dress and animal ears to Fantasy Fest. People spend months planning their costumes for the Mardi Gras style parades, strutting solo or rolling out in groups of up to thirty.

In addition to the overall annual festival theme, each night offers an array of themed costume parties for your selection.
You can be anything your imagination conceives, and you can bet the crowd gets creative!

I borrowed a pirate costume from a Los Angeles friend, model and actress Caitlin O’Connor.

Space Mountain,  Fantasy Fest, Key West (Andy Newman/Florida Keys News Bureau/HO)

2. “Dabbling” in Body Paint

Whether you opt for a playful temporary tattoo or invest in a $400 – $800 award-winning paint job, you’ve just got to give it a go!

Sitting between two beautiful, middle-aged women, having their breasts, neck, and stomachs airbrushed for full coverage — I signed up for an original world map taking over my bare back.

[You’re welcome dad].

The combination of airbrushing and themes exceeds any costume play I’ve seen anywhere in the world. The group of 60,000 — the people at Fantasy Fest in the Florida Keys — do costumes better than any other festival or Halloween festivity I’ve experienced.

32nd Annual Fantasy Fest Toga party at Sloppy Joes, Key West, Florida @StephBeTravel @MattKarsten

3. Shopping and Street Food at the Day Fairs

Because Cuban food and soul food match exquisitely with mechanical bulls, darts, and day prizes, check out the boutiques, food carts, and games.

“Super Heroes, Villains… & Beyond.” Fantasy Fest (Andy Newman/Florida Keys News Bureau/HO)

4. Exchanging Beads at the Parades

Whether you sneak onto a VIP balcony, snag a spot on an elaborate float to throw beads into the crowds, or you’re the one in the mob shake-shaking for some beads, thou shall give or receive beads at Fantasy Fest.

This isn’t Mardi Gras or Brazil’s Carnival. You won’t hear anyone screaming “show us your t*ts* because Fantasy Fest is about being yourself and no one judging you. Plenty of women and men have opted for partial (or generous) nudity, so no one is going to bug you about how much you choose to wear or not wear. You do you.

Fleming Street in Key West, Fla., during the Fantasy Fest Masquerade March. 

5. Drinking Festive Cocktails

By festive, we mean whatever cocktails you want to drink because it’s Halloween. By festive, we’re also talking tropical. After all, you’re on an island on November’s eve with $5 cocktails… on a holiday… at a festival? Must. resist. overindulging.

6. Entering a Costume Contest

All those hours and dollars invested into the New York Fashion Week of Costumes, someone is bound to win thousands of dollars in prizes.

The judges didn’t surrender the booty, but I think my pirate costume was treasure. Corny cuz it’s cute. 

7. Dancing to Live Music and DJs

So much talent! Key West is already infamous for nightlife, it’s no wonder that the best live bands take the stage during the festival. I was wiggle-wiggling with some University of Florida Alumni to “She’s a Brick House,” rockin’ out to Jimmy Buffet’s surprise guest appearance, and getting down to to my favorite Top 40 radio hits.

My favorite party was jammin’ out to this INCREDIBLE live band IDTBand at Sloppy Joes, Key West.

8. Meeting New People

Given the liberal climate, Fantasy Fest boasts some of the friendliest people. I didn’t see a single fight. People would literally just start conversations by telling you that you’re pretty. We’re all just there to have a good time and when you’re in that good of a mood, it’s no surprise you’ll meet new people.

The crowds of Fantasy Fest don’t discriminate. All ages, all races, all shapes and sizes, all sexual preferences, and everyone from broke college students to multi-millionaires .

We have one thing in common: we want to dress up, dance, and be free.

“Aaron Huntsman, left, and William Lee Jones, right, ride the grand marshals’ float during the Fantasy Fest Parade. Jones and Huntsman were selected to preside over the parade because of their contributions to lead the Florida Keys and Florida into same-sex marriage equality. The couple won a ruling from a Monroe County judge overturning Florida’s same-sex marriage ban, but is not wed yet because Florida Attorney General Pam Bondi appealed.” (Andy Newman/Florida Keys News Bureau/HO)

9. Sharing a Cab with Strangers

There’s 75 taxis in Key West and 60,000 people. Thank goodness everyone is so friendly that you can combine squads!

10. Passing Out

If you’ve spent a couple hours getting costume ready, frolicking in the street fairs, throwing beads at the 7 pm parades, and dancing for a few hours (or all night), you’re going to pass out with exhaustion. It’s warm in Florida, you’re wearing an uncomfortable costume (or body paint), and you may have had a couple drinks.

Drink lots of water, have the address to your hotel on hand, and take a buddy or let your friends know when you’re out!

There’s no shame in needing sleep. Take care of your body.

11. Finding Paint All Over Your Sheets

A good loofa will get rid of smaller artwork. Otherwise, try make-up removers, nail polish remover, or water and alcohol mixed to scrub the airbrush off of your body and possessions.

12. Brunch on the Beach

You’re in THE FLORIDA KEYS. The weather is so delightful and all those Christmas carols are going to start chiming post – Halloween. Embrace a good tan, great food, and revel in the resort life post-event madness.

Travel Bloggers Matthew Karsten and Stephanie Be (that’s me!) visit the Florida Keys for Fantasy Fest

13. Repeat

I didn’t meet any other first timers. I guess it’s one of those things you don’t just do once.

Next year’s awesomeness is “Political Voodoo and Ballot Barbarians,” so pull out your red, white, and blue for a do-over.

For more information, check out the Florida Keys and Fantasy Fest official websites:

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