Your Guide to Fantasy Fest Week


Races, parties, parades and more – here’s what should be on your list for Fantasy Fest Week!

With over 50 events (all within walking distance)to choose from, you’ll need a plan of attack.  Your costumes aren’t going to design themselves! We’ve put together a plan for the ideal Fantasy Fest week so you can dress (or body paint) accordingly!


Unlike every other Monday of your life, this one is going to be awesome.  Kicking off over 45 events this week, this Monday will require a superhero…or villain!  The Heroes & Villains 5K run (we use the word “run” very loosely here) starts at 6pm at the Southernmost Beach Café.

Fantasy Fest Week, Heroes and Villains Run



Captain Tony’s Party in Plaid will have you flaunting flannels and kilts because anything plaid goes!  Greene Street will be covered with creative costumes.  And with it being just steps away from our great downtown location, it’s easy to change out your costume and catch another local favorite: TuTu Tuesday at Mangoes.

Fantasy Fest Week, Captain Tony's Party in Plaid



Are you one of those humans who coordinates halloween costumes with your pet?  You’ll be right at home at the Pet Masquerade located at the Casa Marina.  Free to the public, or choose to pay for VIP seating, this event starts at 5:30pm and gets your night started off on the right paw foot.  Proceeds benefit the Florida Keys SPCA.

Fantasy Fest Week, Pet Masquerade



Toga! Toga! Toga!  Sloppy Joe’s may be known for Ernest Hemingway back in the old days, but now it’s known for the biggest Southernmost toga party in the US.  There’s a band, a prize for the best toga, and togas for sale with all proceeds benefiting AIDS Help.   Party starts at 8pm.

Fantasy Fest Week, Sloppy Joe's Toga Party



Get the biggest weekend in Key West started at 1pm with the Bourbon St. Pub Tea Dance! Famous for their New Year’s Eve celebrations, this Tea Dance will be populated with the “Bourbon boys,” drag queens, and celebrities.  Party spans from the pool to the bar to the middle of Duval Street so you’ll have plenty of space to dance to live DJ’s.

Fantasy Fest Week, Bourbon St. Tea Dance



As you already know from our previous “Best Key West Parades” blog, there’s nowhere else you should be on Saturday night except watching the parade.  Cheer on over 50 decorated floats along with thousands of spectators as the parade makes its way through Old Town on Duval Street.  Watch from the street or ask our concierge about rooftop VIP viewing parties to get the full experience.

Fantasy Fest Week, Parade



Family day for those with kids…or the perfect day to sleep in and recover from your perfect week!  Can’t decide where to go?  Check out our top Key West breakfast recovery restaurants – all within walking distance!

Want more tips on Key West?  View our Key West Concierge Tips or check availability at our downtown accommodations for your next Key West getaway!