Fantasy Fest invites businesses, organizations and brands to join the 2026 “Musical Icons and Iconic Musicals” themed magic. There’s a level for everyone to get in on the dream and be seen by tens of thousands of festival-goers leading up to and through the Oct. 16-25 revelry. Sponsorships help fuel the festivals iconic events which in turn support charities, celebrate creativity, and build community.

Sign on for a customizable partnership, or select from a ready-made sponsorship menu for these perks and more:

• Revelers ($1000): Includes free Parade float entry, business listing on Fantasy Fest website and app, 2 official t-shirts and posters, 2 social media posts, and one e-newsletter ad.
• Merrymakers ($2000): Includes all Reveler perks plus use of the Fantasy Fest logo, your logo on listings, more merch, more posts, and two e-newsletter ads.
• Life of the Party ($3500): Host an official Fantasy Fest event with social media and graphics support; plus top tier digital features including a rotating banner ad and special listings in the Fantasy Fest app, plus everything listed above.
• Fantasy Visionary ($5500): Go big with all the above, but with two official events, premium website/app placement, Street Fair space, and radio spotlight love.

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Fantasy Fest 2026 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For all the details e-mail [email protected]. To download the partnership form visit https://fantasyfest.com/pdf/FF2026-Partnership-Opportunities.pdf

He wrote and performs the local anthem “I’m From Key West,” and has been reeling in a following from island stages and streaming platforms for about half a decade. Now, Mike Stack will bring his supercharged energy to the front of the line as Grand Marshal of the 2026 Deep Eddy Vodka Fantasy Fest Parade, set to roll down Duval Street in Key West, FL, on Saturday, Oct. 24.

Possessing a knack for creating catchy, sing-along songs with his unique island-vibe, hip-hop and country blend sound, Stack has cultivated a devoted audience by serving up the salty spirit of life in the Conch Republic with “I’m From Key West,” and other hits like “I Want My Beer,” and “Boat Days,” turning everyday moments into sing-along anthems.

We caught up with Mike ahead of Fantasy Fest to ask a few questions:
Q: This year’s Fantasy Fest theme is “Musical Icons and Iconic Musicals.” If your life were a musical, what would it be called, and who’d play you?
A: This might be too obvious, but if my life were a musical, I’d have to call it “I’m from Key West.” I was born and raised here, and so much of what I do and the music I make comes from growing up on this island. And I’d have my buddy Arron Kutner play me. He’s been preparing for the role his whole life.

Q: What are your top three (or four, or five) annual Fantasy Fest events, and why?
A: A few of my favorites are Goombay because of the culture and food; Tutu Tuesday is just one of those nights where everybody gets after it and has a good time. The parade is always incredible… the floats, the energy, and this year I hear they’ve got a pretty cool Grand Marshal. Honestly, the people watching might be my favorite event of them all. You never know what you’re going to see during Fantasy Fest!

Q: Name three musical icons, living or dead, that you would most love to see in the crowd, cheering you on during this year’s Deep Eddy Fantasy Fest Parade.
A: Bob Marley, Toby Keith, and Mac Miller. Three completely different artists, but all three have influenced the kind of music I love and the music I make. If I saw those three standing together on Duval Street cheering me on, I’d probably have to stop the float and go hang out with them.

“With this year’s Fantasy Fest theme of ‘Musical Icons & Iconic Musicals’, we couldn’t think of a better person to lead the biggest night of Fantasy Fest,” said festival director Nadene Grossman Orr. “Mike has spent years bringing music, energy, and pure Key West spirit to performance stages, and now he’ll be bringing that same energy straight down Duval Street!”
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Fantasy Fest 2026 runs Oct. 16-25 and is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For a full calendar of events, a parade entry form, a downloadable mobile APP and other information including ways to get involved, visit http://www.fantasyfest.com.

Fantasy Fest, Key West, Florida’s annual multi-day costuming party in paradise, welcomes revelers from near and far to turn the island into a living celebration of musical spectacle during this year’s extravaganza, set for October 16-25.

The 2026 Fantasy Fest theme, “Musical Icons and Iconic Musicals” invites fantasy-makers to style themselves at the center of a Ziegfeld extravaganza, follow the call of a disco ball, go Gaga for Ziggy Stardust, embody the Mercury magic, or take center stage as the musical icon – or iconic musical character – of their dreams. The sky’s no limit for this “Swift-ly” moving and “Wicked-ly” wondrous ten-day break from the ordinary.

Here’s a sampling of just some of this year’s highlights. Complete information for events, times, locations, and contest entry links can be found at http://www.fantasyfest.com:

• Fantasy Façades Contest: Creatively transform your home or business for a chance to win cash prizes ranging from $100-$1000. Reflect this year’s theme or channel traditional Halloween ghoulishness! Entry form available Sept. 1; deadline to enter Oct 12.

 

• Oct. 16: The Royal Coronation event to crown Fantasy Fest’s 2026 King and Queen is a dazzling 2-hour stage show at the Coffee Butler Amphitheater that features performances by the intrepid competitors along with local celebrities. Proceeds benefit the Florida Keys SPCA.

 

• Oct. 16 and 17: The Bahama Village Goombay Festival is a two-day, family friendly celebration of island arts and crafts, culture, music and food held throughout Key West’s historic Bahama Village neighborhood.

 

• Oct. 18: That Arena Rock Show at Sunset Pier: A free admission, high-energy, time-traveling theatrical tribute to classic Rock & Roll.

 

• Oct. 19: Mrs. Roper’s Romp: Break out your colorful caftan and signature curly red wig for a groovy “Three’s Company” inspired party at Sunset Pier filled with music, photo ops, dancing, games, and prizes.

 

• Oct. 19: A Green Parrot Beatles Tribute: Jump into your yellow submarine and disembark in the 1960’s for this dress-up dance party with Key West’s very own Beatles tribute band.

 

• Oct. 20: Florida Keys Council of the Arts Fantasy Fest poster-signing party at the La Concha Hotel: Meet the artist, get your poster signed, and stock up on other collectable Fantasy Fest 2026 t-shirts and swag.

 

• Oct. 20: Tutu Tuesday with its annual epic dance party features lights, lasers, and multiple dynamic DJ’s spinning at four different Caroline St. district area venues. Tutu’s required!

 

• Oct. 21: LUV2GLOW PARTY – Rick’s Upstairs on Duval Street transforms into a vibrant universe of fluorescent visuals, underwater-inspired décor, and pulsating house music with immersive glowing environments, DJ’s and live performers. Come dressed or painted to glow under black-lights.

 

• Oct. 21: Pet Masquerade, presented by Florida Keys Media at the Coffee Butler Amphitheater: Costume up with your favorite critter friends at this over the top competition or cheer them on from the audience. Prizes in multiple categories; registration fees benefit the Monroe County Sheriff’s Office Animal Farm.

 

• Oct. 22: The 42nd Annual Key West Headdress Ball, presented by the Key West Business Guild at the Coffee Butler Amphitheater reveals a playlist of out-of-this-world headdresses modeled by their creators along with high-energy entertainment by some of the island’s best talent.

 

• Oct. 22: Sloppy Joe’s 47th Annual Toga Party: Live music starts early and flows late at this revelry, where fantasy-makers can don traditional Roman “drape duds” or create their own 2026 Fantasy Fest theme-inspired versions. Toga costume contest welcomes individuals or groups of 2-4.

 

• Oct. 23: Paparazzi Row is the place to get warmed up and strut your stuff for the camera’s ahead of the Captain Morgan Masquerade March. Dance music will play and local paparazzi, photo booths and selfie stations will be set up to record epic costumed crews.

 

• Oct. 23: The Captain Morgan Masquerade March (aka “Local’s Parade”) brings all creative hands on deck as costumed revelers parade through Old Town Key West, stopping along the route for adult beverage samples provided by selected guest houses.

 

• Oct. 23 and 24: The magnificent mile-long Fantasy Fest Street Fair and Costume Promenade offers revelers an extravaganza of fabulous food, lively libations, arts, crafts and costumes starting at high noon and going into the night.

 

• Oct. 24: The world famous Deep Eddy Vodka Fantasy Fest Parade in Old Town Key West presents a dazzling array of fabulous floats, magnificent marching groups, and cool kinetic contraptions to bring this year’s “Musical Icons and Iconic Musicals” theme to life. An awesome island tradition since 1979!

 

•  Oct. 25: Children’s Day at Bayview Park offers a daytime fest from noon to 5:00pm with games, food, rides, entertainment, arts & crafts, and a costume contest for the kids.

 

• Oct. 25: Don your fabulous feathers for “The Fat Lady Sings” Tea Dance at La Te Da on Duval Street—the final official Fantasy Fest celebration.

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• Oct 26: The 2026 Fantasy Fest theme will be announced.

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“At Fantasy Fest, you can see the spectacle and be the spectacle,” said Fantasy Fest Director Nadene Grossman Orr. “Whether you arrive as a Broadway legend, rock icon, pop superstar, or icon of your own creation, this is your invitation to step into the spotlight and let your imagination take flight.”

Fantasy Fest 2026 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For a full calendar of events, schedule updates, contest details, and a downloadable mobile APP, visit http://www.fantasyfest.com.

“Musical Icons and Iconic Musicals” is the official theme for Fantasy Fest 2026 –Key West, Florida’s annual multi-day costuming extravaganza in Paradise. From October 16-25, those who embrace the magnificence of all things musical can style themselves at the center of a Ziegfeld extravaganza, follow the call of a disco ball, go Gaga for Ziggy Stardust, embody the Mercury magic… You get the idea. The sky’s the limit Lucy, during this “Wicked-ly” wondrous ten-day break from the ordinary.
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Revelers can see the spectacle and be the spectacle—with celebrations including the world-famous Fantasy Fest parade; the Captain Morgan Masquerade March (aka “Locals Parade”) and Paparazzi Row; the exuberant Goombay Festival; Royal Coronation of the 2026 Fantasy Fest King, Queen, and royal court; the dazzling Headdress Ball; kooky Key West Pet Masquerade; a mile-long Duval St. street fair; concerts, pool parties, theater productions, and much more. Fantasy Fest 2026 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For a full calendar of events, visit http://www.fantasyfest.com.

The Florida Keys irrepressibly creative spirit was on full display in an otherworldly spectacle Saturday night as the world-famous Deep Eddy Vodka Key West Fantasy Fest parade made its way down Duval Street, celebrating its 46th year and the 2025 theme, “Bedtime Stories and Magical Monsters.”

Each year, following the parade, prizes are awarded by a panel of judges to multiple “Best Of” entries in a variety of categories, followed by announcement of the following year’s Fantasy Fest theme.

This year, 33 entries competed for $20,000 in prizes, and the winners are:  

• $3000 Best in Entertainment: “Peter Pan” by Blue Heaven.
• $3000 Best in Costume: “Three Little Pigs” by the Lower Keys Fluffers.
• $2500 Best Interpretation of Theme: “One Magical Family” by Guy Hermelin.
• $2000 Best Walking Group: “Angels and Demons” by Daniel Bitnar, presented by the Key West Chamber of Commerce.
• $1500 The Green Parrot’s Best Live Music Award: Greeen House Productions, with “Puff the Magic Dragon.”
• $1000 Best Bicycle Award: “In Your Dreams: Afterlife Waiting Room” by the Southernmost Slow Riders.
• $1000 Directors Choice Award: “Sirens & Sea Monsters: Shipwrecked Dreams” by Pelagic Property Management.

The $6000 Key West Fantasy Fest Parade Grand Prize for Best Overall, presented by The Lodging Association of the Florida Keys & Key West, is awarded to the Key West Kreatives team with their entry “Seuss on the Loose.”
The winning theme for Key West Fantasy Fest 2026, scheduled for Oct. 16-25, is “Musical Icons and Iconic Musicals.” Stephanie Southgate of Key West, Florida, submitted the tuneful idea in Fantasy Fest’s annual “Name the Theme” competition and has won VIP seating with the parade’s judges and organizers for the 2026 Fantasy Fest Parade.

“Whether you imagine yourself at the center of a Ziegfeld extravaganza, follow the call of a disco ball, or go Gaga for Ziggy Stardust, the Tourist Development Association Board of Directors all agree that Stephanie Southgate’s 2026 theme idea absolutely sparkles with exciting possibilities,” said Nadene Grossman Orr, Fantasy Fest Director and President/CEO of We’ve Got the Keys.

Fantasy Fest events wrap up on Sunday with a slate of happenings, including Children’s Day at Bayview Park; “The Fat Lady Sings” Tea Dance at La Te Da Hotel, Restaurant, Cabaret and Bars; Fest finale pool parties held at Island House Resort, Southernmost Beach Resort’s Pineapple Pool, and The Marker, and more. A post-Fest bonus event pops up on Wednesday, Oct. 29, with a Golf Cart Façade Viewing Tour, presented by Greeen House.
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Fantasy Fest 2025 featured more than 100 events citywide and was presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. Visit http://www.fantasyfest.com for photo galleries of 2025 highlights and advance 2026 festival news and information.  

Connie Zemcik, the 2025 Fantasy Fest T-shirt and poster design contest winner greeted Festival revelers and signed posters at the Florida Keys Council of the Arts Official Poster Signing Party on Tuesday, Oct. 21, in the Lobby Tropicado of the La Concha Hotel, 430 Duval St., Key West.

Zemcik, a New Smyrna Beach-based artist and muralist, creates art on buildings, windows, canvas, and now, Fantasy Fest collectibles. She learned about the contest just two days before the submission deadline through an Instagram post. “I integrate all kinds of diverse components together for a living, so I’m used to uniting imagery and dreaming up characters,” she said. “It’s not at all unusual for a client to come to me and describe five or six unique elements they want brought together in an artwork.”
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Her 2025 design, reflecting this year’s Fantasy Fest theme, “Bedtime Stories & Magical Monsters,” bursts with colorful fantasy and Key West flair. The artwork features a radiant mermaid astride a flying “Mother” goose adorned with beads, a rainbow-maned unicorn, a mischievous dragon, and a playful sea monster – all swirling around the iconic Southernmost Point buoy marker. Other whimsical elements include a fairy in flight, a flying fish, a genie emerging from a bottle, and a vivid dreamscape of stars – capturing the imagination and magic that define Fantasy Fest. Fantasy Fest 2025 runs through Oct. 26 and is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For a full calendar of events visit http://www.fantasyfest.com.

Each year Key West guesthouses, businesses and private homes deck out their cribs and compete for cash prizes in the annual Fantasy Fest Fantasy Façade competition. Contestants were challenged to bring this year’s theme - “Bedtime Stories & Magical Monsters”- to life, embrace classic Halloween ghoulishness, or conjure up a creative mix of both. Sponsored by Haunted Key West, the following winners have scored a total of $2500 in prize dollars:

• Best of Fest Prize: Entry #33, Hanks Saloon and Garbo’s Grill at 409 Caroline St., for “Once a Paw a Time.” 
• Hangman’s Choice Prize: Entry #12, The Craig and Gevecker household at 713 Waddell Ave. for “Peter Pan’s Nightmare in Neverland.”
• Ghoulish Grandeur Prize: Entry #16, “We Be Fit” at 1277 1st St. for “Once Upon a Spine – Deadtime Stories.”
• Terrifying Triumph Prize: Entry #30, The Fernandez household at 529 Simonton St., for “Greek Mythology: Medusa’s Garden.”
• Eerie Excellence Prize: Entry #4, The Key West Woman’s Club at 319 Duval St., for “Good Night Key West.”
• Monstrous Masterpiece Prize: Entry #27, The Graves household at 3314 Northside Dr., unit 143, for “Bedtime at the Gravestones.”
• Bucket of Blood Prize: Entry #20, The Doll House on Staples, 2807 Staples Ave. for “Celebrating the Death of Your 30s, Kyle.”
• The Great Pumpkin Prize: Entry #23, The DiFabio household at 2831 Harris Ave. for “Pumpkin Patch.”

And taking the top Spooktacular Showstopper Prize of $1000 was entry #19, the Stockton household at 2912 Staples Ave for “Staples Ave. Cemetery.”

For a listing of all 33 participating entries and their locations, download the Fantasy Fest app, available on the Festival web site.
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Fantasy Fest 2025 is presented in part by the Monroe County Tourist Development Council and We’ve Got the Keys. For a full calendar of events and schedule updates visit https://fantasyfest.com. 

Hundreds of loyal subjects and members of Fantasy Fest royalty spanning decades celebrated with effervescently Key West-style pomp and circumstance at the Coffee Butler Amphitheater on Friday night as Joe Wooten and Cindy Bensen were crowned the new reigning King and Queen of Fantasy Fest.  Mina Valdez and Floyd Jenkins (aka Pepa Mahogany) were installed as Duchess and Duke, completing the 2025 royal court.

Since 1989, Fantasy Fest Royalty have achieved their titles through annual fundraising campaigns that take place over multiple weeks. This year, the four competitors raised a total of $353,538.00 to benefit the Florida Keys SPCA.
Friday’s coronation marks three years since the Florida Keys SPCA took the reins of the Royal Campaign. In 2022, after decades of organizing the competition and benefitting from its proceeds, AH Monroe Executive Director Scott Pridgen and Fantasy Fest board chair Steve Robbins announced it was time to pass the torch. The Tourist Development Association selected the Florida Keys SPCA to take over as planner, organizer, producer, and beneficiary, launching a new era for a competition that has crowned 67 King and Queen pairings and raised more than $5.5 million in 36 years.

Since then, campaign proceeds have enabled the FKSPCA to purchase a fully equipped mobile vet clinic and dramatically expand community outreach – including spay/neuter services, wellness programs, kids’ clubs, animal behavioral training and a Safe Haven program for pets whose owners are in emergency situations, said FKSPCA Executive Director Tammy Fox.

Friday evening’s festivities included dinner and a dazzling two-hour stage show with performances by the candidates and a stellar roster of special guests, co-hosted by Erin McKenna and Bria Ansara. The evening also included a heartfelt tribute to the late Christopher Elwell, 2010 Fantasy Fest King, highlighted by the inaugural presentation of the “Christopher Elwell Royal Award” to 2015 Fantasy Fest Queen Jodyrae Campbell.

The newly crowned Royal Court will appear at multiple 2025 Fantasy Fest events and serve as imperial ambassadors until the 2026 competition, and as Emeritus Royalty in perpetuity.

This year’s “Bedtime Stories & Magical Monsters” themed Fantasy Fest features more than 100 events including Goombay Festival, the wildly enchanting Pet Masquerade, the Captain Morgan Masquerade March, and the world famous Deep Eddy Vodka Fantasy Fest Parade.
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Fantasy Fest 2025 is presented in part by the Monroe County Tourist Development Council. For a full calendar of events and contests visit http://www.fantasyfest.com.

As the City of Key West prepares for Fantasy Fest, some bike racks along Duval Street will be temporarily removed to ensure public safety during the upcoming events. Beginning on October 10th the U-shaped rack will be removed. The racks have already been posted with No Parking signs. The racks will be put back in place after Fantasy Fest.

Bikes left of the racks will be removed and stored by Community Services. Owners of bicycles that must be removed will be required to show proof of ownership and may be charged a storage fee.
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Find nearby bike parking here: https://bit.ly/kwrack