Kenny Chesney has grown from his Knoxville, Tennessee, roots into one of country’s biggest stars. The singer, 40, will show off the locations of his inspiration to the contest winner who wins the trip through MasterCard’s Roots of Rock Sweepstakes.

But even though he’s sold more than 30 million records, this superstar remains self-deprecating. “I’m horrible at playing golf,” he laughs.

Working hard got Kenny where he is today. Hm, why is he a self-proclaimed workaholic?

“It’s just the way I grew up,” Kenny tells me. “I come from a family that works very hard and doesn’t take anything for granted. I’m not a very complacent person. I’m always thinking ahead. I’m always trying to be better.”

Although Kenny says he hates Las Vegas because he isn’t a fan of losing money by gambling, he likes to kick back with friends on his boat in the Caribbean when he has a break from touring.

“It’s a sense of freedom that I don’t have on the road. People that live on boats have an emotional attachment to it. I’m no different. We’ve had a lot of parties on my boat, and we’ve had a lot of fun. But still, being able to go down there and get away from the catering trucks and generators on the buses and the ringing in my ears from all the guitar amps, it’s a great way to get away from it.”

For a Quick Chat with Kenny Chesney, pick up with OK! on newsstands now. Britney Spears: “How I Got My Body Back” is the cover line.

Sound off in the comments below!

Join the conversation