Fantasy Fest: Key West’s Crazy Street Festival

Fantasy Fest
Fantasy Fest in Key West
Key West, Florida

Want to learn about the best-kept secret for street celebrations in the United States? It’s a wild 10 day costume party in October called Fantasy Fest in Key West, Florida.

If I had to describe Fantasy Fest in one sentence, I’d say it’s Burning Man meets Mardi Gras for Halloween on a tropical island. Except in a place where you can also stay in a beautiful B&B surrounded by ancient banyan trees.

A place so diverse that gays, bikers, pirates, artists, strippers and entrepreneurs are the norm, living a motto “One Human Family.” A place where you can watch the sun both rise and set over the ocean every day.

After knowing about the festival for years living in South Florida, I finally made it down to see what all the hype was about with my blogger friend Steph from Travel-Break.net.

Our week was incredibly fun, absurd, and liberating all at once.

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Fantasy Fest Pirate Bash
Shiver Me Timbers!
Fantasy Festival Key West
Super Heroes Showing Some Skin

The Conch Republic

Key West is America’s own little Caribbean island, known as the Conch Republic to locals who fancy themselves a separate country. The island is located at the southern tip of the beautiful Florida Keys.

With certain laws being a bit more lax (like allowing “open containers” on the street) and such a unique blend of people and styles, you actually do feel as though you’re in another land.

Spend an afternoon walking past Key West’s pastel colored homes or browsing some of its 50 art galleries while still never more than a dozen blocks from the sea in any direction.

The whole island’s 1 x 4 miles is navigable by quaint lanes bordered by tropical flora, feeling a bit like a secret garden which you can navigate by foot, bike or moped.

Fantasy Fest Toga Party
Steph is Attacked by Sexy Spartans
Fantasy Fest Parade
Fantasy Fest Parade

Fantasy Fest Vibe

This magical little island gets even wilder when it celebrates Halloween for 10 days at the end of October in an incredible wonderland known as Fantasy Fest… where almost anything goes.

Bring out any piece of your character (or a different one every night)!

During the festival venues host their own special events. These celebrations create an entire world within themselves, worlds that you are encouraged to join in! They pull together a combination of local cuisine, talented artists, and fundraising for various local charities.

This collaboration makes each event take on a life of its own, feeding everyone’s creative inner-child that you’ll leave the festival feeling closer to.

There are costume competitions, AIDS fundraisers, family-friendly parades, drag-queen contests, and more.

Pirate Party
Pirates
Alien Costume
Intergalactic Alien Invasion

Intergalactic Freak Show

The theme for 2015 was the All Hallows InterGalactic Freak Show, and it certainly lived up to its name. This small town welcomed 60,000 freaks, free spirits, and aliens from all over the country.

People spend months planning out their costumes (or lack thereof) for the multitude of themed parties that happen throughout the week. I got into the spirit of things by packing 3 different costumes myself — Greek God, Dirty Pirate, and Intergalactic Alien complete with full-body paint job.

One night Steph and I found ourselves at Irish Kevin’s annual Fantasy Fest 80’s party when who should crash the stage but Mr. Margaritaville himself!

Jimmy Buffett (ok, maybe not the real one) picked up a guitar and played along with the band for a few songs as the rest of us danced like no one was watching.

Just a typical evening at Fantasy Fest in Key West.

Exploring Ireland
Is that Jimmy Buffett?
Fantasy Fest Queen
King & Queen of Fantasy Fest 2015

Fantasy Fest Events

Some highlights of Fantasy Fest include The Coronation Ball where the Conch King and Conch Queen make an appearance. They win this royal title by having raised the greatest amount of funds for AIDS Help.

In 2007 they raised over $200,000 and since 1989 almost $2.6 million has been donated.

Goombay is a two day street party held in Key West’s Bahama Village neighborhood. It’s named after the goatskin drums that generate the party’s rhythms and celebrates the heritage of Key West’s large Bahamian population with food, art and a lot of dancing.

Other popular events include the Zombie Bike Ride, Pet Masquerade, Anything But Clothes Party, Rum Barrel Pirate Bash, Airbrush Expo, Sloppy Joe’s Toga Party, and much more.

You can find a full listing of events on the Fantasy Fest Website.

On the last day, the festival culminates with the Fantasy Fest Parade down the town’s main Duval Street spanning the 1 mile cross-stretch from the Atlantic to the Gulf shore.

Key West Parade
There’s No Place Like Home
Pirate Bash
Arrrrrgh! Rum Barrel Pirate Bash

Fantasy Fest Tips & Advice

While basically an extended adult costume party at the end of October, Fantasy Fest doesn’t always fall on Halloween itself. It did in 2015, but that’s not always the case.

There’s some nudity at Fantasy Fest, but that’s not all it’s about. You’ll find people of every race, age, body type, sexual-preference, and career here too. A celebration for judgement-free and open-minded people.

With only 75 taxi cabs and 60,000 people during the event, finding a taxi isn’t always easy. Renting a bike might be a good option for getting around, provided you don’t drink too much.

No Fantasy Fest experience is complete without some body paint. Airbrush artists from around the country set up shop to make your dreams reality. Prices range from $100 to $800+ depending on how intricate the work is.

Need a cure for your killer hangover the morning after? Grab a bite to eat at Blue Heaven or some strong cuban coffee at Cuban Coffee Queen.

Clown Costumes
Psychotic Clowns
Fantasy Fest Costumes
Don’t Mess With These Two…

Getting There

So how do you get to this crazy party called Fantasy Fest in Key West? Fall down a rabbit hole? Hope a tornado picks up your farmhouse in Kansas? Fortunately you can just drive 160 miles South from Miami on Highway US1.

The road trip to Key West from Miami is a beautiful drive over endless bridges across the Florida Keys islands, flanked by the Atlantic Ocean on one side and the Gulf of Mexico on the other.

A quick 45 minute puddle jumper flight from Miami or Ft Lauderdale airport directly to the island is also possible.

Good Places To Stay

We stayed at the beautiful Casa Marina Resort on the edge of the water. But I’m a big fan of AirBnB too. If you haven’t yet, make sure to read my article about how to find cheap hotels.

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So if you’re looking for a good party, and wild photos of crazy and scandalous costumes, you have to check out Fantasy Fest sometime. I hope I’ll see you there next year! ★

Travel Planning Resources For Key West
Location: Key West, Florida
Official Website: FantasyFest.com

Packing Guide

Check out my travel gear guide to help you start packing for your trip. Pick up a travel backpack, camera gear, and other useful travel accessories.

Book Your Flight

Find cheap flights on Skyscanner. This is my favorite search engine to find deals on airlines. Also make sure to read how I find the cheapest flights.

Rent A Car

Discover Car Hire is a great site for comparing car prices to find the best deal.

Book Accommodation

Booking.com is my favorite hotel search engine. Or rent apartments from locals on Airbnb. Read more about how I book cheap hotels online.

Protect Your Trip

Don’t forget travel insurance! I’m a big fan of World Nomads for short-term trips. Protect yourself from possible injury & theft abroad. Read more about why you should always carry travel insurance.

Recommended Guidebook: Lonely Planet Miami & The Keys
Suggested Reading: The Key West Bucket List

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Fantasy Fest: Key West’s Crazy Street Festival. More at ExpertVagabond.com
Fantasy Fest: Key West’s Crazy Street Festival. More at ExpertVagabond.com

READ NEXT: Ultimate Key West Road Trip

Florida Keys

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Hi, I’m Matthew Karsten — I’ve been traveling around the world for the last 9 years as a blogger, photographer, and digital nomad. Adventure travel & photography are my passions. Let me inspire you to travel more with crazy stories, photography, and useful tips from my journey.
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24 thoughts on “Fantasy Fest: Key West’s Crazy Street Festival”

  1. Your photos are absolutely *incredible*!!! Thank you for sharing. It makes me miss Key West :) The last time I was there, I accidentally ended up living on a sailboat for a few days… :D

  2. Thank you for this great article. This will be my 15th year for Fantasyfest. It is so much fun and you are so right about people of ALL kinds getting together and having a blast!

    • Awesome Lori, you’re a regular! I met many people like you who’ve been visiting this event for 10+ years in a row. Have fun this year at Fantasy Fest 2016!

  3. Some may be offended by the Indian Chief costume though I am sure no offense was intended. The influence of Mardi Gras is evident. Street festivals are common in other states as well. Some have religious relevance.

  4. This looks like an absolute riot. It’s great to read about festivals I’ve never heard of to add to the list.

  5. Very colorful party, great pics, is the idea of carnival. Is the time that people feel comfortable to take over the streets and party all night long. It’s fun to see people from many parts of the world getting together to party.

    2 tips is the carnival of Guanaja (honduras Caribean island) and the biggest carnival in the world in Rio de Janeiro.

  6. I’ve know about Fantasy Fest for years, but never seem to be in the right place at the right time. We haven’t spent enough time in South Florida either for that matter. Snorkeling is very high on our travel agenda (in Playa Del Carmen as I write this), so it is inevitable that we will end up there for some time underneath the waves. Hopefully we can also time it right for a trip into crazy land. Better pack some non essential travel items I guess!

  7. I hadn’t heard of this before, but it looks really fun! There was a guy in one of the photos with a wicked witch costume that made me chuckle.

  8. What a splash of colors! I have always wanted to attend such a festival since a long time for the sheer liberating feel it can provide. One of my friends has been attending this festival since the past 10 years!

    • That’s the beauty of Fantasy Fest Frank, you don’t need to be either to have a good time! Young & old, fat & skinny, everyone is welcome here.

  9. I have been waiting for this article ever since you mentioned that you would be attending. Love all the colorful costumes. I need to get my butt down there one year for this. It’s pretty high on my bucket list.

    • So glad I finally made it down there for Fantasy Fest. I think I’ll be dressing up for this festival every year now! I met people who’ve been attending it for 20 years.

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