Rocking the Keys: Howard Livingston's Trop-Rock Journey from Coal Miner's Son to Island Music Maestro

From the heart of Kentucky's coal mines to the sun-kissed beaches of the Florida Keys, trop-rock singer Howard Livingston has charted an extraordinary course. Just 18 years into his music career, Livingston's 11th album, “House Down by the Sea,” is making waves. He's a local staple, headlining at Boondocks Grille & Draft House on Ramrod Key and Sugarloaf Lodge, not to mention his star turn at the Florida Keys’ 2023 bicentennial bash.

Livingston's tunes, like “I’m Living on an Island” and “Blame It on the Margaritas,” are more than just catchy—they're the anthems of the island lifestyle. And get this: the man's not just a Trop Rock Music Awards Entertainer of the Year; he's also a philanthropic mixologist! During shows, he whips up margaritas with a quirky, motor-powered machine and auctions them for Keys charities.

This Cumberland, Kentucky, and Marion, Indiana, native turned Chicago engineering student, and diesel parts manufacturer, first got hooked on the Keys in the mid-80s. "I was blown away by the Keys. I realized I was home," he reminisced. Fast forward to now, and he's a proud Summerland Key homeowner.

But Howard Livingston's more than just a musician; he's a giver. Along with his wife, Cyndy, and a close-knit group of friends and fans, they've raised a whopping $1 million for children’s charities like Care Camps. His life philosophy? “It's a great day when you get to wake up on an island. I've found paradise.”

When he's not strumming his guitar, you'll find him at Boondocks, enjoying the family vibe, or indulging in Italian cuisine at Roostica on Stock Island. And when it's time to unwind? It's family time at home, with grandkids, his dog Anderson, and never missing a sunset. That's the Livingston way – living and loving life in paradise.