Trop-rock singer Howard Livingston, son of a Kentucky coal miner, started playing Keys-inspired music only 18 years ago and has just released his 11th album, “House Down by the Sea.”
In the Lower Keys, Livingston and the Mile Marker 24 Band are frequent headliners at Boondocks Grille & Draft House & Miniature Golf on Ramrod Key and at Sugarloaf KOA Lodge. He also headlined the “200 Years of Paradise Kick-off Concert” celebrating the Florida Keys’ 2023 bicentennial.
Known for his “I’m Living on an Island” and “Blame It on the Margaritas,” among other popular feel-good island lifestyle tunes, Livingston is a Trop Rock Music Awards Entertainer of the Year winner.
He’s also known for cranking out tart and tangy margaritas during his shows, using a one-of-a-kind giant margarita machine powered by a 1952 Johnson outboard motor — and auctioning them off to benefit Keys charities.
Livingston grew up in Cumberland, Kentucky, and Marion, Indiana, earned a trade school scholarship to study engineering in Chicago, and “always had a guitar in the corner.” In Chicago, he launched a business manufacturing parts for diesel engines.
He first began coming to the Keys in the mid-80s, staying on rented sailboats and exploring the island chain.
“I was blown away by the Keys. I realized I was home,” Livingston said, subsequently spending “every waking moment” calculating how he could live in the island chain.
During a work meeting in China, he composed his now-famed song “Living on Key West Time.” By the 1990s he had purchased property on Summerland Key, where he lives today.
Through his music, Livingston and wife Cyndy, with friends and supporters, have raised more than $1 million for children’s charities including Care Camps, which sends kids with cancer and siblings to specialized summer camps.
His motto: “It's a great day when you get to wake up on an island. I've found paradise.”
Where he dines: Boondocks for the great food and drinks, dog-friendly space and family atmosphere with mini-golf and an open-air market. Roostica on Stock Island for Italian food and pizza.
Where he explores: The backcountry to enjoy the out-islands, sandbars and incredible marine life.
How he relaxes: At home with wife Cynderella, grandkids and dog Anderson. “We love our island town and never let a sunset go unnoticed.”
Howard Livingston, pictured here at his home, has just released his 11th album, “House Down by the Sea.” Photo: Cyndy Livingston
Livingston and his wife Cyndy are pictured along with engineer Jake Burns in Jimmy Buffett's Shrimp Boat Sound Studio in Key West while recoding his new album. Photo: J.L. Jamison
The Livingstons and their dog Anderson enjoying the view from their home on Summerland Key. Photo: Rob O'Neal