Kenny Chesney on His Ocean Obsession, Literary Escapes, and the Places That Keep Him Grounded (Exclusive)

Kenny Chesney may be one of the most recognizable names in country music, but when he talks about being on the road—or more specifically, when he talks about getting off it—his answers are down-to-earth. He has performed for millions, headlined stadiums for decades, and built an empire of beach-infused songs that audibly evoke postcards from paradise. Yet it’s the quiet moments—those spent with a notebook, a boat, and the ocean stretching to infinity—that seem to move him most.

“Anywhere with a beach, where I can just unwind my mind,” he tells Travel + Leisure, when asked where he escapes to. “But I love Italy, too, and getting lost, eating pasta, and wandering around completely unseen. To me, when you can be in a place and absorb the people and the culture without changing it, that’s heaven.”

That sense of balance—between global fame and personal peace–anchors Chesney’s new book, Heart Life Music, out Nov. 4. It’s a reflective and revealing collection of stories from a small-town Tennessee boy who became one of the biggest touring artists in the world. Fans will get a rare glimpse of that side of him at the Miami Book Fair, where he’ll headline the “Evenings With” series on Nov. 16 alongside his co-writer and longtime collaborator, Holly Gleason.

Heart Life Music in Hemingway’s studio in Key West.

Kenny Chesney

“Florida has been such a part of my journey,” says Chesney, who will be headlining Tortuga Music Festival in Fort Lauderdale next April alongside Post Malone and Riley Green. “We kick off so many tours in Tampa. We have played keg shows we announced the day before at Sloppy Joe’s and the Hog’s Breath in Key West. As a child, my family would go to Daytona Beach, and there was that unbelievable concert we threw ‘just cause’ on the Florida/Alabama border.” 

He continues, “I actually signed a contract with my soul in West Palm Beach, behind the Coral Sky Amphitheater, after the opening show of my first real headlining tour. That night, I promised the universe I wouldn’t give 90 percent, but I would give every last speck to doing this. It’s a total commitment to create, to show up and perform, to really give people songs that can move them in their lives.”

It’s a promise he’s kept. With nearly three dozen No. 1 hits on the Billboard Country Airplay Chart and more than 30 million albums sold, Chesney’s career has been built on hard work, open-hearted songwriting, and an enduring relationship with his fans, known affectionately as “No Shoes Nation.” And while he’s long associated with sun-soaked anthems, his connection to the ocean runs deeper than any possible marketing narrative.

At Hemingway’s House in Key West.

Allister Ann

“My favorite island is the one with the least people,” he says. “But my love of the ocean really began with my mother taking me to Myrtle Beach as a boy. In my book, the chapter ’Something Fried’ is all about how much I fell for the ocean, the culture that happens in beach towns, and how happy it made my mother. To me, the water is so vast, there’s room to let your mind unwind and your imagination just drift.”

He adds, “If I had my guitar, a few notebooks, something to drink, and a copy of Old Man & The Sea, I could disappear into watching the sun move across the sky and counting stars for days and days.”

That Hemingway mention isn’t incidental; literature is another deep passion for Chesney. “I love books and reading,” Chesney says. “I also love audiobooks when I’m in the sauna, because I can really sink into the moments that are being created by the words. Hemingway really captured my imagination… the sentences are so powerful, his sense of self. But even in being such a strong personality, when you read something like The Old Man & The Sea, the bond between the young man who helps Santiago and this elderly man who will not relinquish his dream of catching a giant Marlin hits me in the heart.”

With Kenny Chesney

Favorite hotel? 

The Reef, Myrtle Beach, South Carolina.

Best jet-lag cure?

Ice tub.

Go-to room service order? 

Salmon, green beans, spinach or carrots, bottled water.

Favorite destination? 

Anywhere with an ocean.

Favorite book or author? 

Hemingway, especially The Old Man & The Sea.

Reading and reflection are two constants for this artist who spends much of his year on the move. “Figure out where I’m going to work out, especially on tour… that’s one thing that anchors me and keeps my head right,” he says. “Beyond that, just having a sense of where I am. I like to walk or ride a bicycle around where I am, exploring. And if I can find a great, truly local place to eat, that’s even better, because that’s tapping into the culture and the people of wherever I am.”

As a traveler, he packs light but with intention. “My Laird Hamilton protein bars, my journal, and my saltwater and sun-faded and frayed Boston Red Sox cap,” are three things that always make it into his bag.

When asked about his most unforgettable trip, he answers, “When I bought my first boat, me, my boat captain, Ben, my other boat captain, Brian, and my manager, Dale Morris, drove it from Fort Lauderdale to Georgetown in the Exumas. It was the most beautiful trip. The water and the sky were beautiful, and time just stopped. We drank a lot of beer; I wrote in my journal a lot.”

When he disconnects on vacation, he has a ritual that sounds like serenity itself. “I’m waking up on a boat, jumping in the ocean, watching the sun come up… get back up on the boat, dry off, put the music on, make a protein shake, and just hang. Maybe, depending on how long I’ve been off tour, I might pull the guitar out of its case and let the sun hit my skin while I play my guitar.”

Kenny playing guitar on the bow of his boat in Caribbean.

Allister Ann

His travel list remains simple and sunlit. “I’ve never been to Australia,” he says. “I want to go see the beaches there. That’s on my bucket list.”

Pivoting back to his upcoming appearance in Miami, Heart Life Music emerges as perhaps more than a memoir. For Chesney, it’s a genuine meditation on connection and purpose. “Holly Gleason, my co-writer, has done the Miami Book Fair two or three times, and she says they’re such smart, curious people who attend,” he says. “I love the idea that it’s all different kinds of writers, novelists, Latin and island writers, business leaders and political people, historians, pop culture people and scientists. To be part of all that, it’s not just humbling, it makes me feel like my book has a place in this world.”

That idea—that we each really do have a place in the world—is what has always made Chesney much more than just a chart-topper. He’s a traveler in the truest sense —always chasing new horizons, with a guitar and a notebook in hand.