A Labor Day in Paradise: Celebrating Jimmy Buffett in Key West

Close your eyes for a moment and picture it:
The late summer sun is dropping low over Mallory Square. A salty breeze drifts off the water, carrying the sound of steel drums and laughter down Duval Street. Everywhere you look, there are flip-flops, margaritas, and wide smiles—the kind of scene Jimmy Buffett himself would’ve called paradise on earth.

This Labor Day weekend, Key West once again becomes Buffett’s island stage with the 2nd Annual Just a Few Friends Festival (August 29 – September 1, 2025). It’s not just a celebration—it’s a homecoming for the songs, the stories, and the spirit Jimmy left behind.

🎶 The Rhythm of the Weekend

It begins on Friday, when the State of Florida officially proclaims Jimmy Buffett Day. Bars pour extra-strong boat drinks, locals share stories of Jimmy’s Key West days, and the streets feel alive with that one particular harbor energy.

Saturday brings the kind of adventures Jimmy wrote about: rum tastings, sunset cruises, and a big night at Sunset Pier with Roger Bartlett, the very first Coral Reefer guitarist, reminding everyone how it all started.

But it’s Sunday that steals the show. A Second Line Memorial Parade marches down Duval, a sea of feathers, beads, and music leading the crowd straight to Truman Waterfront Park. As the sun dips behind the harbor, the free Party in the Park lights up the night with Howard Livingston & the Mile Marker 24 Band, Nadirah Shakoor, and a few surprises from Buffett’s closest friends.

By Monday, the island takes a deep breath. A mustache contest, happy hours, and a sunset serenade from Will Kimbrough close the weekend with a smile and a song. Come Monday, it feels like Buffett never left.

🌊 More Than Music

This festival isn’t just about the party. It’s about giving back—with proceeds supporting Reef Relief, the Bahama Village Music Program, and the Key West High School Marching Band. Last year alone, over $34,000 was raised.

And because it’s Key West, you’ll find more than music. There’s Brewfest running alongside, with 60+ breweries pouring ice-cold pints on sandy beaches, plus book signings, art markets, and those unforgettable Key West sunsets that make you believe in magic.

✨ Why You Belong Here

If you’ve ever sung along to Margaritaville, dreamed of a cheeseburger in paradise, or just needed an excuse to get lost in island time—this is your weekend.

Key West doesn’t just celebrate Jimmy Buffett. It keeps his spirit alive in every song, every cocktail, every laugh echoing down Duval Street. And this Labor Day, you’re invited to be part of the story.

👉 Plan Your Weekend at JustAFewFriendsKeyWest.com

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