A couple riding motorcycles at 801 Bourbon's Fantasy Fest

801 Bourbon’s Fantasy Fest facade.

By Shayne Benowitz

When it’s time to write about Key West Fantasy Fest, I usually begin by saying something about “madness descending on the island” or “let the insanity begin!” And this year that’s precisely the plan with the theme “Habitat For Insanity.” We are right in the midst of it! The Curry Mansion has transformed into a mad house and 801 Bourbon is now the Dragasylum. How can things NOT get crazy?

Of course, this week is a nonstop party, if that’s what you’re looking for, and there’s a brand of crazy for everyone. However, it’s probably humanly impossible to attend every shindig. Here are my picks for the best parties of the week—you’d be insane to miss out!


Couple in costumes having fun at the Red Fest in Key West

Red Party @ Fogarty’s

This one is a perennial favorite, especially amongst the Fury Key West crew. The theme is simple, don as much or as little red as you like and hit the town! The massive outdoor patio will be packed and a DJ will be spinning to get you moving.


Friends wearing costumes at the Toga Party in Key West

Toga Party @ Sloppy Joe’s

This is a classic. Whether you squeeze into the crowd at Sloppy’s or just mosey up and down Duval Street, tie on a sheet, throw a reef in your hair, and head out!

Prohibition Party @ The Porch

One of Key West’s newest hot spots will be hosting this gangster and flapper-style soiree. Perch above the mayhem at the Porch, and get debauched at this speakeasy wine and beer bar. Bonus: Key West Burlesque will set the tone with dancing girl entertainment.


Friends in costumes  joining the parade in Key West

Masquerade March

Throw on a costume, grab your friends, and take it to the streets with this much-loved walking parade. Free drinks and snacks are handed out along the route to keep your spirits and energy high. The parade finishes on Duval Street where the fun will only be starting!


Fantasy Fest Parade

This is the culmination of all the madness! The Fury Key West crew will be partying at Stephen and JB’s Duval Street locale complete with balcony viewing. I’m looking forward to seeing how the floats reflect this year’s theme! Surely, it will be mad! See you there!

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Last Updated 10/29/2021