Will Kimbrough - Live in the Chart Room

This may become one of the most talked-about moments of the entire weekend.

The experience begins with a chef-curated beachfront brunch at the Pier House from 10:00–10:45 AM, complete with a Bloody Mary or mimosa overlooking the water in the relaxed style that defines Key West mornings.

Guests will then move into the legendary Chart Room Bar.

Long before stadium tours and sold-out amphitheaters, this tiny wood-paneled hideaway inside the Pier House was where Jimmy Buffett found his footing in Key West. He played for drinks and tips here in the early days, surrounded by fishermen, wreckers, writers, bartenders, and the colorful cast of characters who helped shape both his music and the island mythology that followed. The room remains largely unchanged — a living piece of Key West history and one of the most iconic spaces connected to Buffett’s story.

Inside this intimate setting, acclaimed songwriter and longtime collaborator Will Kimbrough will perform a rare up-close set filled with music, storytelling, and personal reflections. Kimbrough co-wrote “Bubbles Up,” the final Jimmy Buffett song released posthumously, and has spent decades creating music alongside some of the most respected names in Americana and roots music.

This will not be a traditional concert.

It’s a rare opportunity to sit inside the room where so much of the story began and experience the music and memories in a way that simply cannot happen from a stage.

All guests will receive a limited-edition commemorative keepsake created exclusively for this experience — a unique memento from an unforgettable Key West moment shared with just a few friends.

Attendance is extremely limited and expected to sell out quickly.