Preparing for Key West Fantasy Fest 2019 – Get your tickets


Started in 1979 by a group of Key West locals, Fantasy Fest has grown over the years to a costume party extravaganza, featuring over 60 wild costume parties throughout the course of 10 days.

To get the maximum fun out of any event that you attend, you will need to do a little preparation in order to fit into the individual mode of each party. That means, finding, buying or creating an appropriate costume for each event.

This year’s theme is “In Tune But OFF Key,” which leaves a lot of room for individual interpretation. This blog will feature some of the events that require a payment or a ticket booked in advance and what kind of outfit you will need to participate each.

Photo by Flickr user Michel Churi

On Monday, you’ll find the Kinky Carnival at First Flight (formerly Kelly’s), 301 Whitehead Street. You won’t be allowed to enter unless you are wearing a kinky costume. There is a $35 cover charge at the door and tickets cannot be ordered in advance. There’s an open bar from 8 to 11pm, a DJ, pole dancing and aerials. It’s the 21st anniversary celebration in 2019, so you know they must be doing “kinky” right!

Photo by Flickr user Brian Lin

Also on Monday is the Heroes and Villains 5K Run/Walk at 6 pm, starting at the Southernmost Cafe, 1405 Duval Street. Be bold, be brave, be awesome, and prepare a hero or villain costume to inspire you across the finish line. The first 400 to register get a puzzle piece medal and there are costume prizes for every age category — from the tiniest participant to the most senior. The registration fee is $25 in advance, or $35 the day of. Get all the details and register here.

If you’re energized and ready to go after your walk/run, celebrate at the After Party, the Southernmost Beach Luau, also at the Southernmost Beach Cafe. There’ll be a Key West style pig roast and plenty more food and drinks. Your $45 ticket includes the food and one drink per person. Sign up in advance at

Photo by Flickr user Brian Lin

Tuesday brings the eleventh annual Tutu Tuesday! The pre-party begins with a drink at Mary Ellen’s (420 Applerouth Lane) and a tutu party costume parade through downtown. People are encouraged to create “walking tutu floats,” but remember that no motorized floats are allowed. Parade stops include Mary Ellen’s, First Flight, Tiki Bar and General Horseplay. Tickets are $35 and cover a shot at each of the stops, and your entrance to the esteemed Tutu Party at General Horseplay, 423 Caroline Street.

Photo by Flickr user Michel Curi

“The 11th annual Tutu Party is celebrating the glory of the tutu and all of its wonderment.”. Doors open at 7pm. If you haven’t got your wristband from Mary Ellen’s pre-party, you can purchase one here for $20, beginning on Saturday, October 20. The rule is: no wristband, no tutu, no entry. Order tickets online here.

Photo by Flickr user istolethetv

On Wednesday, the very popular Pet Masquerade gets underway at the Waterfront Park Amphitheatre. If your pet is in Key West with you, if you’re missing your pet left at home, or if you just plain love animals, this is the event for you! There are four categories for entrants, including an adorable junior section. This is a chance for big bragging rights as you costume yourself and your pet and work out some schtick for the stage.

The $25 entry fee to participate on stage benefits the Lower Keys Friends of Animals. Registration starts at 4 pm and the show gets underway at 5:30. It’s free to watch and food and drink are available for purchase. Free seats are available at this brand new venue, but feel free to bring your own blankets and lawn chairs.

Photo by Flickr user Brian Lin

Wednesday is the 27th Annual Original Key West Hommemade Bikini Contest, being held this year at the Smokin’ Tuna Saloon, 4 Charles Street. Put your creativity to work and pay only a $10 entry fee for a chance to compete for $5,000 in cash and prizes. It’s as simple as it sounds: homemade bikinis only! Doors open at 7pm and the contest begins at 8. Watching is free unless you want to want to pay for one of a limited number of VIP Backstage Passes that include a meet and greet with the contestants, an open bar, and light food. These can be purchased here.

We’ve included only a few of the fabulous events of Fantasy Fest 2019. Watch for our next blog on Prepping for Fantasy Fest Part 2 which will feature free events that you will want to have a costume for. For all of the events, check out the Fantasy Fest website at