Key West doesn’t just host festivals. It lives them. And if you’ve ever wondered who’s actually pulling the strings behind the island’s biggest celebrations and most beloved traditions, 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 stories behind the stages, 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.

Southernmost Beach Resort has been part of this story for a long time. What makes that partnership work?

Southernmost Beach Resort was one of the very first hotel partners. The Southernmost pool party was actually the first pool party ever on the Key West Songwriters Festival schedule. It’s the OG. Some of the most legendary “you had to be there” moments have happened there. A couple of years back, Jelly Roll – who was headlining the Festival that year- surprised everyone by getting on stage to sing his Hit Songs with the writers we had in that Songwriters Round. People didn’t know what they were witnessing, but now they sure do.

I’ve had a relationship with Southernmost Beach Resort through all these years. Laurayne (Complex Director of Sales and Marketing) and Anthony (Complex Marketing and Events), who are currently there, are phenomenal. They’re the first people I go to when I have a new idea. When we decided to expand the Kick Off party for the Key Lime Festival event on Duval Street for the first time, setting up a stage in front of the Avalon, they were like, “Sure, that sounds great. Let’s try it.”

And they come back to me with ideas, too. They just said, “Hey, our Songwriters party is on Derby Day — can we do a Derby theme at the start of our beach show?” Heck yeah I said: “Let’s make everyone wear hats.” They’re full of good ideas that create joy, and that’s why we keep building together.

Photo credit: Virginia Wark

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 Southernmost Beach Café, and our sister property, The Marker Key West Harbor Resort, as both will be serving up island favorites.
• 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 Southernmost and The Marker. 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 – and yes, the World Famous Key Lime Pie Eating Championship will once again take place at Southernmost Resorts’ South Beach.
• 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.

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.

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.)

Finish this sentence: A Key West festival experience is…

Magical. Everyone’s welcome to come as they are. We’re silly, we like to have fun, and we do things differently here. We give people a joyful experience they just couldn’t have any place else.

Plan Your 2026 Festival Getaway

Southernmost Beach Resort is more than just a place to stay; we’re part of the island’s history and its celebrations. For a month‑by‑month look at everything happening this year, check out our 2026 Key West Festivals: An Insider’s Guide to the Year’s Top Events.

Book your 2026 stay and experience the “OG” festival magic for yourself. #somolife