Getting Ready for the Fest – A peek behind the scenes with Key West Fantasy Fest Producer Nadene Grossman Orr

​When it comes to over-the-top costuming extravaganzas, nothing compares to Key West Fantasy Fest, a legendary mashup of parades, outrageous themed parties, and jaw-dropping pageantry that turns the island into one big, fantasy playground for 10 days and nights each year. Not bad for a festival that started more than four decades ago just to spice up the sleepy fall season at the end of US1.

In 2017, Fantasy Fest experienced a vibrant resurgence when Nadene Grossman Orr, winner of the 2003 Fantasy Fest Queen title and head of the production company “We’ve Got the Keys” – known for producing large-scale, city-wide events - seized an opportunity to present her vision to the Monroe County Tourist Development Association’s Board of Directors. Her pitch hit the mark, winning her the contract to produce the Fest. With a vision that celebrated both community ownership and bold creativity, she and her team have since reimagined Fantasy Fest for a new era – without losing sight of its rich and irreverent roots.

Q: What inspired you to pursue the Fantasy Fest production contract?

Nadene: I arrived in Key West two weeks before Fantasy Fest in 1991 – it was my induction! With that timing and my wiring, it was pretty inevitable that I would go full immersion, and for years I was an enthusiastic costumed participant with my friends. Working as a hotel concierge back then, I also had to be well informed about the festival for our guests. I began volunteering with AIDS Help – now A.H. Monroe, helping them run the King and Queen campaigns. The pre-festival, behind-the-scenes community effort, raising funds, lifting each other up, was so inspiring to me. That was my Fantasy Fest path, and the foundation for my passion to become its director.
 
Q: What were some of your original goals?

Nadene: Fantasy Fest really has an enormous financial and emotional impact here. It supports multiple local non-profits along with businesses, hotels and guesthouses, and most importantly, the hundreds of individuals who rely on this annual celebration to pull their finances out of the summer doldrums. Knowing first hand the importance of this to so many, my goals included reigniting our sense of local ownership, ramping up creative, super imaginative costuming, and making it culturally relevant for future generations while still embracing its glittery legacy. 
 
Q: How is Fantasy Fest funded?

Nadene: Sponsorships and event grants from the Monroe County Tourist Development Council! Sponsorships mostly come from Florida Keys hotel partners, businesses, and brand partners who are featured throughout the festival and who get to host the official Fantasy Fest events.
 
Q: How many events does Key West Fantasy Fest typically encompass? 

Nadene: More than 100! So friends, please support the sponsors—where you stay, party, and even what you sip—because that helps keep so many Fantasy Fest events free and thriving. Our team-produced events like the Fantasy Fest Street Fair, Captain Morgan Masquerade March, and the Deep Eddy Vodka Fantasy Fest Parade are all made possible thanks to that support.
 
Q: What kind of team does it take to pull this off? 

Nadene: I have a full-time team of five at We’ve Got the Keys, and Fantasy Fest is our biggest project of the year. Some of our other events include the annual Key Lime Festival, Key West Songwriters Festival, and Taste of Key West. We start planning each Fantasy Fest before the previous year’s festival ends—that’s when we choose the next year’s theme!

As we get closer to October, we bring in more staffers to help with logistics like the Street Fair, parades, and retail operations. And we couldn't do it without around 150 volunteers who help us get the Masquerade March and Fantasy Fest Parade smoothly and safely through the streets. It’s a true team effort powered by passion.

Q: What makes your team tick? 

Nadene: Creativity, camaraderie, and an unshakable sense of purpose. We thrive on energy, pride, patience, and mutual support—plus coffee, chocolate, and cheese! Seriously though, we love what we do, and we love this community.
 
Q: What have been some of your greatest challenges?

Nadene: Taking over in 2017 came with big dreams and the vision to rebrand and take the legacy event in a new creative direction. Then, just weeks before the festival was to begin, Category 4 Hurricane Irma hit. All hands were on deck to help with community support and clean up – and of course Fantasy Fest was put on hold while City and County leadership determined if infrastructure could even be restored in time to welcome so many visitors back to the island after such a devastating storm. But we got the official “GO”, and while it was a challenge to pull off, being able to help restart the local economy and bring joy to the community after the devastation made it so worth it.
 
Then came March of 2020. Navigating through COVID-19 forced us to reimagine everything. We canceled the parade and street fair. We held a “Community Wins” campaign online to raise funds for locals in need. Then 2021 brought a new variant and again no full-on festival – but we modified and adapted. Fantasy Fest has always been about creativity, reinvention and resilience.
 
Q: Did you get to keep your 2003 Fantasy Fest Queen crown?
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Nadene: YES!
 
Q: Do you wear it shopping? To special events?

Nadene: Ha! Its heavy! It’s been a while since I’ve worn it … very special royal engagements, and the occasional coronation! I do love to see my fellow royals in the Holiday Parade each year donning their royal attire! 
 
Q: Words of wisdom to Fantasy Fest-ers?

Nadene: We always say: pace yourself! Download the app, map your plan, and prepare for a wild ride.
Fantasy Fest 2025 takes place from Friday, Oct. 17 through Sunday, 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, contests, schedule updates, a downloadable mobile APP and fun ideas on how to get involved, visit http://www.fantasyfest.com.