Caribbean Cowboy

Such a true believer is Chesney in the transforming power of island vibes that he feels compelled to share what he’s discovered not only with his crew, whom he transports down there en masse at the end of each long, grueling tour (he sold 1.2 million tickets last year, more than anyone but Prince), but also with his fans. “I want to bottle up all of it and take it on the road,” he says.

That would explain Marley, the 265-pound blue marlin he caught off the Northern Drop in the BVIs that goes on tour (in a custom case that cost 10 grand) and sits at the side of the stage as a talisman for the team. “In my live show people really connect with the whole vibe,” says Chesney, who used to use Bob Marley’s “Three Little Birds” as his intro music. “It’s not just a song on the radio.”

An inevitable consequence of his Caribbean fixation is that Chesney fans are increasingly taking vacations to the Virgin Islands. “They’re following in droves,” he says. “It’s double-edged. I want them to buy into the lifestyle, but there used to be a time I could dance on the bar and howl at the moon. There are too many cameras now. Thank God I got a boat and there’s a lot of little islands.”

He still likes to howl, though, at the drop of his old straw hat. “After I played the University of Tennessee with Kid Rock two summers ago, the two of us got on my bus, stopped at Krystal for 20 burgers, went to the airport, got on my plane, flew to the Virgin Islands, got on my boat and went to the BVIs. The night after we played for 65,000 people at UT we played four hours for 60 or 100 people at Foxy’s. We played all his stuff, all my stuff and every Marley song we knew.”

For all the carrying-on and the spontaneous tiki bar gigs, the islands are primarily a place for Chesney to decompress, get away from music for a while and read. In the grand tradition of Caribbean literature, he says Old Man and the Sea is his favorite Hemmingway book (“reminds me of my grandfather”), and it’s recently prompted him to catch up on To Have and Have Not.

But there comes a time during the long vacations when he can’t resist picking up the guitar. Be As You Are is his first singer-songwriter album, a scrapbook of tunes that he says were never even meant to be recorded, much less released as a theme album. However, one of the fruits of achieving success on Nashville’s terms by producing monster hits like “She Thinks My Tractor’s Sexy” is that you eventually get to share the stuff that’s a bit closer to your heart, more about where you’re really coming from.

“It used to be my home away from home,” says the Tennessee native of his Virgin Islands getaway, “but now it’s my home more than anyplace else. Without the island lifestyle I wouldn’t have the energy or the inspiration to accomplish what I have. Being able to shift gears has given me clarity and focus. The people, the boat, the bars, the fishermen, the music, the blue chair, the rum — everything helped make that happen.”

On that tidy note, the luncheon interview concludes and Chesney cracks open his fortune cookie: “A much-needed vacation will bring a great deal of enjoyment.” But he already knew that.

Caribbean Travel & Life is the magazine for anyone in search of the perfect tropical getaway. Each issue presents expert insider’s advice on where to find the Caribbean’s best beaches and attractions, its finest resorts and spas, liveliest beach bars and activities, and its friendliest people.

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