When he's in country-music-superstar mode, Kenny Chesney counts Tim McGraw, Kid Rock and NFL quarterback Peyton Manning among his big-name buddies. But when he's relaxing near his home in the Virgin Islands, Chesney maintains a decidedly lower profile—even hopping behind the bar to serve cocktails at a local watering hole. Says pal Will Grimsley: "He can really work the blender."

With his golden tan, flip-flops and hang-10 grin, Chesney looks more the part of beach bum than country king, which suits him just fine. Although he nabbed the Country Music Association's Entertainer of the Year prize in November and his 2004 concert ticket sales were second only to Prince's, the 36-year-old musician known for his sexy size-29 Levi's (see box) and fist-pumping, rock-arena-style shows happily escapes Nashville for island living when he's not working. "Here, time hangs like a hammock," says Chesney, who composed his new album, Be as You Are: Songs from an Old Blue Chair (due Jan. 25), at the Spanish colonial-style Virgin Islands home he bought in '03. "When I'm on the road, I'm always thinking. Everything revolves around a schedule. Down here, it's such a deep breath for me."

So much so that writing Songs from an Old Blue Chair proved to be a healing experience for Chesney, who first retreated to the Virgin Islands after his engagement to healthcare administrator Mandy Weals, 35, ended four years ago. "I was in a really pissed-off part of my life," he says. "I was horribly hurt. Anytime now that I start feeling bad, I take myself mentally back to that chair"—a worn wicker seat—"with my feet in the sand." It was there, after falling asleep on New Year's Eve four years ago, that Chesney says he awoke to a life-altering realization: "The next morning the sun came up over the hill, and that's when I realized that I was going to have to make myself happy. I came back with a whole new outlook. Now I feel much more in control."

Not that the Luttrell, Tenn., native has completely abandoned his country-boy roots. On Christmas he returned to his Grandma Lucy's Knoxville home and indulged in her signature red-velvet cake. The only son of a hairdresser mom and teacher dad (he has a younger half sister), Chesney didn't discover his musical talent until he picked up his first guitar as a freshman at East Tennessee State University, where he earned a marketing degree. In 1993 he released his first album to lackluster sales. "Early on, I was a punching bag for what not to be," he says. "The day I stopped trying to be George Strait and started being Kenny Chesney was the day things turned around for me."

Some turnaround. Chesney's last album, When the Sun Goes Down, went triple-platinum and was the best-selling country album released in '04. "Literally, it was not long ago that I had 15 or 16 guys on a 12-bunk bus," Chesney says of his early tours. "Now I wake up in my stateroom [on his tour bus], look out the window and see a sea of [tour] trucks and buses. It's just like how it looked back when I saw Van Halen in Knoxville a long time ago. It happened to me!" Today Chesney counts Van Halen rocker Sammy Hagar among his close friends. "I love the guy," says Hagar. "He came down to [Cabo San Lucas] for my birthday, brought his whole band and crew, and played for 3 hours and 40 minutes without charging a penny at the door. You have to love what you are doing to do something like that."

Currently gearing up for the kick-off of his spring tour in March, the single Chesney is also looking ahead to adding a family to his breezy island lifestyle—though not quite yet. "I can definitely see myself married with kids," he says. "It may be like Tony Randall, when I'm 70. I'm not ready to say I'm locked down for life. But I do feel like I'm getting closer to letting some of those walls down again."

By Michelle Tauber. Andrea Billups in the Virgin Islands

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