The Chart Room Bar at the Pier House Resort served as more than just a watering hole. It was a chaotic theater of smugglers, treasure hunters, and local officials where deals were struck and stories were forged. Tom Corcoran, the bartender who would later find fame as an author, welcomed Buffett with a free Heineken, anchoring him to a community that prioritized island philosophy over professional ambition. Buffett began playing for tips in local haunts, eventually meeting Phil Clark, a bartender whose life of illicit Caribbean adventure served as the direct inspiration for the song "A Pirate Looks at Forty."

More than five decades later, the bar retains its original atmosphere. This September 3–7, the "Just a Few Friends" festival will host a series of storytelling events in the space. Carol Shaughnessy, a former writer for the Coconut Telegraph who was once engaged to Clark, will moderate conversations detailing the island's wilder era. Alongside these oral histories, musician Will Kimbrough—a longtime Buffett collaborator—will perform in the room where the singer once busked, offering fans a rare look at the unvarnished origins of the Margaritaville mythos.