Behind Key West's Biggest Festivals with Nadene Grossman Orr

Key West festivals aren't just events. They're experiences that spill into the streets, onto the beaches, through pool parties, and out onto the water, turning the whole island into a stage. If you've ever wondered who makes that magic happen, you're about to meet her.

Nadene Grossman Orr is President and CEO of We've Got the Keys and the creative force behind Taste of Key West, Key West Songwriters Festival, Key Lime Festival, and Fantasy Fest. We sat down with her to talk about how she got here, what's coming in 2026, the moments you couldn't plan if you tried, and what makes Key West festivals feel different from anywhere else.

How did you get started in Key West's festival scene?

It all started about 27 years ago when I was a cocktail waitress at the Hog's Breath Saloon, and Charlie Bauer was starting up the Key West Songwriters Festival, which is celebrating its 30th year this year. It started small, just a few shows at the bar and maybe 125 tickets for the performance space upstairs. I was also working as a concierge at the Hilton, and I said to Charlie, "I bet we could do a really cool show over on the Hotel’s waterfront pier at Sunset.  If the hotel supports us by hosting more Songwriters, we can grow the festival and have bigger shows."

He gave me an inch, and I took a mile.

I kept pushing: let’s do something at the Green Parrot; Sloppy Joe’s wants a show; more hotels and guest houses will support more artists and we can do shows poolside, sunset decks, and on their beautiful beaches. We did shows out on the boats, and those original shows we did on the Fury catamaran turned into the “Commotion on the Ocean,” which is still a trip they do every night of the week now. When I started, there were eight artists. Now there are around 250.

How important is partnership to the festival experience?

While our sister property, Southernmost Beach Resort, is the OG, home to the very first pool party on the Songwriters Festival schedule, The Marker has carved out its own role in the festival magic.

For Songwriters, everyone wants to see the headliners, but the real magic happens at the smaller, more intimate shows. The poolside sets at places like The Marker are where we're putting the new artists, the ones people will be bragging about seeing "before they were famous." That pool party gets so packed you can't fit another body over there, and that energy is what makes it unforgettable.

Laurayne (Complex Director of Sales and Marketing) and Anthony (Complex Marketing and Events), who are currently at The Marker, are phenomenal. They come to me with ideas, and I go to them. It's that kind of partnership.

For Key Lime Festival, The Marker is home to our Key Lime Cocktail Contest, which has become one of the festival's signature events. And during Fantasy Fest, The Marker's Barbie's Pink Pool Party for Breast Cancer Awareness is a pool packed with pink energy, a costume contest, and Fantasy Fest fun, all for a good cause.

When I think about what makes a great hotel partner, it comes down to people who get it. They understand that festivals aren't just about filling rooms. They're about being part of the experience.

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The 2026 Insider Scoop: What to Watch For

• Taste of Key West (March 23, 2026): Look for the new restaurants first—the ones you haven’t tried yet. But always save room for the “old faithfuls” like John Correa at Cafe Sole; his Portobello soup has sold out for 30+ years. And don't forget to stop by The Marker Key West Harbor Resort's booth where they’ll be serving up island favorites. Photo credit: Taste of Key West

• Key West Songwriters Festival (April 29–May 3, 2026): Since it began, cities have been trying to duplicate it. But this is the original. Everyone wants to see the headliners, but the real magic happens at the smaller shows—like the poolside sets at The Marker and  Southernmost Beach Resort. That's where we'll place the new artists you'll hear next year. The festival has been a starting point for household names like Luke Combs, Kacey Musgraves, Florida Georgia Line, Jamey Johnson, Hardy, Ernest, Lee Brice, Randy Houser, and Maren Morris ... and the list goes on.
   
• Key Lime Festival (July 1–5, 2026): This year is America's 250th anniversary. What's more American than Key Lime Pie? We're adding something special to celebrate. The Key Lime Cocktail Contest will once again take place right here at The Marker, and the World Famous Key Lime Pie Eating Championship at Southernmost Beach Resort's South Beach. Photo credit: Virginia Wark
   
• Fantasy Fest (October 16–25, 2026): This year’s theme is “Musical Icons & Iconic Musicals.” The street fair is back on Duval, and don’t miss the “Drive Down the Keys” Pit Stop Party scavenger hunt; it’s something new that ties the whole island chain together.

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One moment that has stuck with you?

Hearing Chris Stapleton sing in a small, 150 seat Theater. It was 2005, and I can close my eyes and still hear his voice, this is way before anybody knew who he was. When he started singing, I don’t think anybody took a breath. The room was so quiet. People were stunned. I still get goosebumps.

Once you hear the stories that inspired these artists to write their songs, it's never the same for you.  You will hear them on the radio or performed live by the Artist who recorded them … but you will always remember the magic of hearing it performed by the writers themselves.

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Festival Tips

• Download the app. If there's an app associated with the festival, download it. It's the easiest way to stay in the know.
• Book early. Get the schedule and your tickets in advance. They do sell out.
• Stay close to the action. You never know who you might see—or what you might miss—if you’re too far from where the music, costumes, pool parties, and late‑night moments unfold.
• Ask the locals. Ask the front desk, your bartender, the concierge, or your cab or rideshare driver what they love to do.
• Plan for flexibility. You’ll stumble upon something and think, “This is cool, I have to stay here.” Let the island guide you.
• Costume up. For Fantasy Fest, one costume is not enough. (And if you forget yours, there’s even a costume shop right at Southernmost Beach Resort.)