Duval Street Party with the Landshark Band

Step into a piece of Parrot Head history 🌴🎶 as Duval Street comes alive for a special recreation of the legendary 1998 Meeting of the Minds street concert.

The evening kicks off with Caleb Hogan, whose acoustic set channels the storytelling, humor, and early spirit of Key West that helped define the music and the lifestyle.

Channeling the look and spirit of ’70s Buffett, Caleb will also host the first annual Bubba Look-Alike Showdown, presented by Hogfish Bar and Grill. Contestants bring their best looks, moves, and personality to the stage—and the crowd decides the winner. It’s part tribute, part competition, and all in good fun as the audience becomes part of the show.

At 7:30 PM, Gary & the Landsharks take over Duval Street, delivering the high-energy, sing-along set that brings it all home. This nostalgic throwback captures the raw, unfiltered energy of those iconic Key West nights when the music took over the street and the crowd became part of the show.

Break out your vintage Parrot Head gear, throw on those old-school tees, and come ready to sing every word 🍹 This is one of those rare moments where past and present collide—bringing longtime fans and first-timers together in the heart of it all.

While the concert is free and open to all, Ultimate Friend and Best Friend VIP badge holders will have priority upfront access near the stage—putting them right in the center of the action.

✨ Free and open to the public

🍹 Come early · Stay late · Sing loud

Brought to you in part by Milagro, Sloppy Joe’s, Irish Kevin’s, and the Tourist Development Council.