Coconut Telegraph Trolley Tour

Climb aboard the Coconut Telegraph Trolley Tour for an unforgettable narrated journey through the Key West landmarks that shaped the music and the lifestyle.

Hosted by JAFF co-founder Sean Krikorian and longtime Key West insider Carol Shaughnessy—the original writer of the Coconut Telegraph—this experience is grounded in real history, personal connection, and the stories behind the stories.

This comprehensive island tour goes beyond the walking version, covering more ground while diving into the places, characters, and moments that helped define an era.

Roll past the bars, streets, and hidden corners that inspired legendary songs, including his former home in New Town, a stop at Fausto’s Food Palace for a chocolate milk (a nod to his famous cure for a long night), Dog Beach and Louie’s Backyard—just steps from where he once lived—and out to Stock Island for a stop and a drink at the infamous locals’ watering hole, Hogfish Bar & Grill.

Along the way, you’ll hear firsthand stories, insider perspectives, and the lasting influence of island life that shaped both the music and the culture.

Created exclusively for Just a Few Friends, this is a one-of-a-kind experience you won’t find any other time or place—an authentic look at the Key West that inspired it all.