Key West’s sensational and internationally renowned Fantasy Fest roars into its 40th anniversary with an “In Tune But Off Key” theme that encapsulates the wildest musical periods of our lives. Key West’s Finest is here with our guide to special events happening on and off Duval. Party, drink, shop, and eat your way through what’s shaping up to be one of the best Fantasy Fests yet! 

Fairvilla Costume Extravaganza
524 Front St | Fairvilla’s Sexy Things 
Oct 19th-31st  11AM – Midnight

Couldn’t bring a costume trailer with you? No worries. Fairvilla’s Sexy Things is your costume headquarters. Tutus. Head pieces. Craft masks. Leather creations. And funky accessories galore! The entire Team will be on hand, ready to assist with any and all outfitting needs. Be sure to make your way to the back for some of the naughtier selections you might want to try. You know? For the after parties at your hotel room. 

Capt Ron Wolek Bodypainting

Glam Up with Captain Ron Wolek
524 Front St / Fairvilla Beauty Garden
Oct. 20th – 26th | 11AM – Midnight

Renowned celebrity makeup artist Ron Wolek and the Wolek Studios team turn the courtyard on Front Street into the enchanted Beauty Garden for incredible transformations. Shine like a painted god or goddess with one of this “Captain’s” illustrious looks for any of the week long festivities. We recommend his incredible talent for the Zombie Bike Ride, Friday Masquerade March and Saturday Bud Light Parade revelry.  Capt Ron also has advanced coupons for the Green, Red, White, Blue and other special parties. Stay in tune or go off key with a more shocking one of a kind design that’s sure to turn heads in downtown Key West. Book ahead or visit him the same day.

Trunk Show

Fantasy Fest Trunk Show
7001 Shrimp Rd | The Green Pineapple at The Perry Hotel
Oct 18th | 5.30-8.30PM

The Green Pineapple teams up with the award winning Perry Hotel at its second location for an incredible trunk show experience. Gather among Key West’s most exciting artists with bubbles and bites. View the works of rapidly rising brands including Barbara Sage’s kaleidoscopic Whimsy Key West and Jenny Belcourt’s Zacasha Jewelry and bohemian accessories. As an added bonus, attendees can enjoy 20% off their purchases. Certainly, not a bad way to wind down a Friday evening before heading off to Matt’s Stock Island Kitchen & Bar for some of the best food in town.

Goombay Island Wine Tasting
300 Petronia St | ViV Wine Bistro
Oct 18th | 12-9PM

Wine connoisseurs Laurent and Julie present three festive island wines and two signature cocktails to kickoff Goombay celebrations! Nestled in the heart of the historical Bahama Village, ViV’s prime location and quaint outdoor seating offers up spectacular views of Goombay’s street fair and parade extravaganzas. Indulge in the specially curated vino selections and savor the phenomenal happy hour food offerings. We recommend tasting their cheese boards and perusing the in-store offerings for the best edible souvenirs to take home.  

Zombie Brunch

Zombie Brunch
3593 S Roosevelt | La Trattoria Oceanside
Oct. 20th | 11AM – 3PM

One of Key West’s most popular destinations for authentic Italian cuisine continues its gastronomic tribute to the undead! Conveniently located within walking and biking distance to the start of this year’s Zombie Bike Ride, La Trattoria Oceanside is serving up its all you can eat buffet for under $30! This year also features an on site body and face painter to present your zombified best just before kickoff. Eat from the continuously replenished selections and order from the full bar! And if you must have a heaping side of brains at this family friendly affair, ensure it’s at least al dente. 

Duck, Duck, Booze Pool Party
7001 Shrimp Rd | The Perry Hotel
Oct 21st | 12-4PM

The festivities may be centralized downtown, but don’t count Stock Island out of the fun! The award winning Perry Hotel opens its pool and spectacular display of rubber duckies to the public for this poolside bash. Presided over by DJ Buggy and sponsored by Brown Sugar Bourbon, this afternoon encourages party goers to sport creative costumes and enjoy all the samplings of the chic marina view and hotel grounds.  Be sure to come hungry as this hotel is famous for it’s fantastic island bites.

Wicked Lick

The Wickedest Ice Cream Licks
335C Duval |Wicked Lick
11AM – 11PM

If you don’t lick it, someone else will! One of Key West’s latest crazes is the liquid nitrogen ice cream offered by Wicked Lick on Duval. This street side parlor encourages patrons to BYOB. That’s right! Your favorite liquors  – and coffee – can be refashioned into a wide array of craft ice cream flavors. Be sure to try the limited edition Candy Corn and Black Cherry Bourbon versions being rolled out in time for the week long celebrations! You may not be able to take bottles or cups everywhere you go, but ice cream is fair game.  

Southernmost Beach Cafe

Beach Bash: Blast from the Past
1405 Duval | Southernmost Beach Café
Oct 22nd | 2-5PM

Get ready for an oceanside aquatic frolic with the incredibly popular and local favorite band Patrick and the Swayzees! Drink and food specials run throughout the event at this popular tourist destination as you learn – or remember – how to do the Twist, score at beach blanket bingo, and sport your boldest polka dot bathing suits and psychedelic tie dye creations. It’s a welcome nod to our groovy past summers in the sun.  Great food will be served at the cafe so bring your appetite.

The Marker Resort

The After Party
200 Williams St | The Marker Waterfront Resort
Oct 27th | 12-4PM

The party continues well into the final day of Fantasy Fest. However, perhaps a bit of R&R? The Marker Waterfront Resort hosts one of the best local friendly pools. On hand will be an entire I.V. team ready to nurse you back from even the gnarliest of hangovers.  We recommend trying the Marker’s delicious watermelon salad with blackened KW Pink shrimp or handmade brick oven pizzas while you recuperate.

La Te Da Tea Dance

Fat Lady Sings Tea Dance
1125 Duval | La Te Da
Oct 27th | 4PM

It’s not over till the full figured woman sings! Capping off the week of festivities, is this last official event of Fantasy Fest 2019. In addition to being one of the island’s most exclusive hotels, La Te Da hosts Key West’s historical Sunday Tea Dance. What is a Tea Dance? It’s a casual afternoon dance event complete with ballads from illustrious divas: Donna Summer, Grace Jones, Tina Turner, Cher, and Madonna. The poolside restaurant area is transformed into a lively and packed celebration as scores of attendees send off another year of fantasy with the greatest hits. 

These are a small sampling of the wild and wacky events happening during Fantasy Fest. Check the full schedule on fantasyfest.com.

Here are our hotel recommendations for last minute reservations: keywestfinesthotels.com

Check out my tips for Fantasy Fest here: YouTube

Be safe, behave and keep it clean in public (it’s not Hedonism weekend)!