Party in the Park: Tribute to Bubba

After the Second Line March winds its joyful way through town, the celebration continues at Party in the Park. Settle in on the Truman Waterfront lawn for an easygoing evening of live music, local flavor, and island energy as the festival comes together to celebrate the spirit of Key West and the songs that were born here.

The evening features performances by Howard Livingston and the Mile Marker 24 Band, Will Kimbrough, and Mac McAnally—three artists whose music and songwriting helped shape the sound and storytelling of the Gulf Coast and the Florida Keys. The night unfolds in true island fashion with a relaxed, come-and-go atmosphere on the waterfront lawn, perfect for kicking back and letting the music carry you through a beautiful Key West evening.

Howard Livingston and the Mile Marker 24 Band are the Florida Keys’ beloved trop rock troubadours, known for breezy island storytelling and songs that perfectly capture life in the Keys. Will Kimbrough, a celebrated songwriter, producer, and guitarist who collaborated closely with Jimmy Buffett in recent years, brings soulful musicianship and heartfelt storytelling to the stage. Mac McAnally—Grammy-winning songwriter, longtime Coral Reefer Band member, and one of Buffett’s closest musical collaborators—adds the unmistakable voice and musicianship behind many of the

songs that defined the coastal sound of the region.

Beyond the music, explore the Key West Artisan Market Island Time Market & Food Court, featuring a curated collection of local artists, makers, and chefs. Browse tropical art, handmade jewelry, island-inspired gifts, boutique fashion, and delicious bites from food trucks and local vendors. You’ll also find full bars, specialty drink stations, and plenty of space to spread out on the lawn as the evening unfolds against the backdrop of a spectacular Key West sunset over the water.

Grab a cold drink - may we suggest a Milagro Margarita - sample delicious eats, shop a little, and find your spot on the lawn to soak up the tropical sounds. Whether you're dancing, relaxing, or simply taking it all in, Party in the Park is the signature gathering of the weekend—best shared with just a few friends.