By Jamie Collins

For Trop Rock musician Howard Livingston, life in the Keys each day is like winning the lottery.

On a recent episode of the PBS show Samantha Brown’s Places to Love, he said, “Everybody here wants to be here.” 

That is true of his own past, a story which leads him from Chicago to the Keys and continues with a successful band and musical career. 

“Everybody loves [living in the Keys]. They love the sun, they love the ocean. They love the island life, if you will, and that’s what makes this place so special – the people are incredible,” he said to Brown as the sun went down while playing guitar at picturesque Fort Zachary Taylor State Park. 

Livingston is one of the very people he spoke about to Brown. He didn’t perform music professionally until he moved to the Keys from Chicago permanently in the ’90s and bought a house close to Key West. It was Southernmost sailboat living in the ’80s that originally made him fall in love with the islands.

You can hear that love in songs like “Livin’ on Key West Time,” “Blame it on the Margaritas” and “Local on the Eights” – a song that describes pretty much every snowbound person’s dreams of paradise.  

Howard Livingston and the Mile Marker 24 Band, complete with a horn section, started its season at Boondock’s Grille and Ale House in December. They perform there every few weeks.

“It’s kind of our home base,” Livingston told Lower Keys Live. “We just played the Key West Half Marathon. It’s one of my favorite things to do.”

Of performing with his friends, he said it’s like going to a party every gig. “And then as you’re leaving, they hand you a check as you walk out the door.”

As far as the genre, Livingston said he and his band have been fortunate to play mostly original music inspired by the likes of other Trop Rock stars like Kenny Chesney and of course, Jimmy Buffett.

“I think Jimmy is the king of that. He’s so many other things too, but he’s an incredible songwriter and a great businessman,” Livingston said.

He is backed on stage by Tim McAlpine, Rick Cleaver, Hal Howland, Hulber Gagliardini and Mark Rose. The band has a following too, which raises money for local charities. It’s called the Southernmost Coconut Castaways, and it’s a “friends club” which prides itself on “Serving Community Roles with Caribbean Souls.” Since 2011, the 501(c)3 has been hosting social hours and gatherings called Jump Ups. Its home bar is the Smokin’ Tuna Saloon in Key West.

Livingston has been featured on the Today Show, CBS Early Show and Good Morning America. He’s also performed with Little River Band, America, Hank Williams, Big n’ Rich, Keith Urban and Tim McGraw. 

 “I want another thirty years of stuff just like today,” Livingston said. “I pinch myself every morning. I don’t want any more or any less – just as many days like this as I can get.”

To learn more about Howard Livingston and the Mile Marker 24 Band, visit or follow him on Facebook. For more information about the Southernmost Coconut Castaways, visit