Key West, Florida, USA
If you’re a fun-loving hedonist who enjoys a masquerade party, Fantasy Fest and its 10-day revelry will be your Costume Ironman.Read More...
The Fantasy Zone in Old Town stretches along Duval Street from Front to South Streets and across the intersecting roads to Simonton and Whitehead Streets.
Key West is both physically and morally about as far from the American South as you…Read More... Close
Key West is both physically and morally about as far from the American South as you can get while still being in the South. It’s more free-flowing, rum-soaked Caribbean than it is flag-waving American and the highlight of the year is this ten-day celebration when life masquerades as a festival. If you love getting dressed up in multiple costumes, all in the same day, for multiple days, this is your perfect habitat. I’m naturally drawn to Fantasy Fest because I’m a Halloween baby, but I haven’t made it yet. Friends of mine return every year like a religious ritual.
If you love getting dressed up in multiple costumes, all in the same day, for multiple days, this is your perfect habitat.
Show your fashion sense at the infamous homemade bikini contest. The Hog’s Breath Saloon is the location for the Wednesday Beach Party where bare is in.
If you fancy getting dressed fancy, head to the Green Parrot Bar. On Thursday evening, you can connect with a more stylish and sophisticated crowd (two words you don’t hear much at Fantasy Fest). Okay, frankly, it’s not sophisticated as it’s mostly intricate body painting which means bare is in again. The Green Parrot is a great place to meet locals.
Don’t forget you’re in the Caribbean. The Friday Street Fair turns Duval Street into a tropical marketplace with great food and arts and crafts from the region.
The best Florida stopover point, functionally and culturally, to Key West is Miami. Once you fly from Miami, you’ll arrive at the Key West airport that is four miles from Old Town. You can also drive to Key West that is a 159-mile drive from Miami which is one of the great American roadtrips. With three times as many people coming to the island (as many as 75,000 attendees) as live on the island, it’s essential to book your accommodations early and be prepared for high prices, although weekdays are a little less expensive. Some people stay at Marathon, one hour away, as the motels are less expensive there.
Started by two Key West businessmen who wanted to accelerate the start of the traditional peak winter season, Fantasy Fest probably rivals Mardi Gras as America’s most free-for-all hedonistic party for those 20, 40, 60, or 80. While the roots of the event match Key West’s gay mecca demographic, over time, the audience has grown more mainstream but, beware, there’s a “try-sexual” flavor that still adds a spicy twist to the affair. Fantasy Fest isn’t for everyone, but for those who love it, they swear by it and make the trek every year attracted by the combination of balls, costume competitions, body painting, homemade bikini contests, and the infamous camp parade where people just let it all hang out, literally.
The festivities begin at the two-day Goombay Street Party Celebration in Bahama Village, but the kickoff highlight is the first Friday night Royal Coronation Ball for the Fantasy Fest King and Queen, known as the Conch King and Queen (Key West considers itself the Conch Republic, sort of its own banana republic) who’ve raised the most money for a Key West AIDS organization. Some of the other annual events include the Tuesday Headdress Ball, the Wednesday Pet Masquerade and Parade, the outrageous Thursday Pretenders in Paradise costume contest, the Masquerade March, and Sloppy Joe’s Bar’s toga party with bed sheets and laurel wreaths being required attire. If you’re an extrovert who enjoys a good party, you will be in your element.
One of the Wildest Parades in North America
The finale parade starts on Saturday night and the revelry goes all night into Sunday. It’s an oddly surreal event as it’s one part small-time America, one part David Lynch film, and one part gay pride parade. Duval Street is the main drag and “drag” is the operative word as you’ll rarely see a more cross-dressing procession in your life. Some of the highlights are the flamboyant floats and merry-raising marching bands. There’s a little flavor of Carnival with the slinky costumes full of feathers and Caribbean drums. You’ll get that Mardi Gras flavor by watching people throw beads at their favorite processions. And, there’s a pretty plentiful supply of alcohol flowing throughout the finale evening. It’s not necessarily an event made for most families. On the other hand, you’re likely to see quite a range of generations on parade as there are lots of older drag queens who live in Key West year-round having retired from Soho or South Beach years ago.
Relax and Enjoy Key West
Given how long this festival is and the number of nights of parties, some of the best advice is to enjoy the adventure and beauty of this part of the world. There are many snorkeling and diving shops that can take you out to enjoy the underwater fantasies (although be careful doing that if you’ve had anything to drink the night before). Ernest Hemingway’s Home and Museum is an essential tourist stop which is open daily from 9-5 along Whitehead Street. Renting a bike, and using it, is also a great way to burn off some of last night’s alcohol and see what Key West has to offer. All in all, Fantasy Fest is almost like an oddball family reunion given how many people make the journey each year. Just know that it’s a very welcoming and friendly environment for people of all sizes, ages, colors, and genders.