Cayman Smith-Martin

For Cayman Smith-Martin, Key West music isn’t something he discovered. It’s part of his story.

Born in George Town, Grand Cayman, Cayman was raised in Key West and graduated from Key West High School in 1994. Music and creativity surrounded him from an early age, giving him a firsthand connection to an era of Key West that continues to influence his work today.

Over the years, Cayman has developed his own place within that musical tradition as a singer, guitarist, songwriter, and collaborator.

Growing Up in Key West

Cayman’s connection to Key West music reaches back to his childhood.

His father, B.J. Martin, was part of the colorful Key West community of the era. The family’s circle also crossed paths with musicians and artists who were helping shape the island’s identity.

Among those connections was Jimmy Buffett, who was a family friend during his early Key West years. That history would eventually take on new meaning in Cayman’s own musical career.

Growing up around that world gave Cayman something that can’t easily be recreated: a personal connection to the people, places, and stories behind the music.

Finding His Own Island Sound

Cayman has built a sound that draws from many of the musical styles heard around Key West.

Reggae is an important part of that mix, but it isn’t the whole story. His performances move easily through rock, ska, funk, roots music, and Caribbean-influenced sounds.

That range is especially evident with The Skank, a Key West band fronted by Cayman and Jeff Clark. The group’s music blends reggae rhythms and harmonies with influences ranging from ska and funk to rock.

Cayman’s work also extends beyond performing other people’s music. He has participated in Key West’s singer-songwriter community and performed his original material in settings dedicated to showcasing local songwriting.

Keeping the Roots Alive

In recent years, Cayman has taken on another role: helping preserve a piece of Key West’s musical history.

With Cayman & the Mango Men, he has revisited the early music of Jimmy Buffett. The focus isn’t simply on playing the biggest hits. Instead, Cayman digs into the songs connected to Buffett’s early years and the Key West culture that helped inspire them.

For Cayman, that music is personal.

He knew Buffett through his family’s connection to him and grew up surrounded by some of the same Key West culture that found its way into those early songs.

During one tribute performance, Cayman made his intentions clear: audiences weren’t there for the usual “Margaritaville.” They were there to hear Buffett’s roots.

That distinction says a lot about Cayman’s approach. He isn’t trying to recreate a version of Key West he learned about later. He’s sharing music connected to a place and time he remembers.

Part of Key West’s Continuing Soundtrack

Today, Cayman remains an active part of the Key West music community.

He performs on his own and through collaborations such as The Skank and Cayman & the Mango Men. His work connects the island’s musical past with the musicians and audiences keeping that culture alive today.

In a town where music is constantly evolving, Cayman Smith-Martin brings something especially valuable to the stage: a sound shaped by Key West and a perspective rooted in having grown up here.