Caribbean Cowboy

But Chesney is eager to put a bit of distance between himself and the pack.  He doesn’t want to be taken for an opportunistic Parrothead wannabe  — he’s not a tourist, he’s a local now. “I don’t want people to think this is a weekend with Jimmy Buffett,” he says.

Yes, he’s sensitive to the issue of influence when it comes to Buffett. “We have a lot in common in the way we live our lives,” says Chesney, “and when I listen to his earlier records I see he was a dreamer, too. But as much as I love him, he’s got nothing to do with my new album.

“Look, I realize ultimately people are going to compare this record to his,” Chesney continues, “but it’s so much about me and my feelings and a life-changing period I’ve been through. I wrote these songs about people I know with kind hearts and deep souls. I’m setting their lives to music. I’m not just listening to ‘Margaritaville’ on a boat for a weekend. This is not a case of trying to steal style points.”

So does that mean we’re not going to see a chain of Kennyville tiki bars opening up any time soon? 

The idea has been floated. “I never say never,” says Chesney, “but I’m not ready to commercialize myself that much just yet. That would take a little bit of the heart out of it for me.”

Chesney’s Caribbean journey began during vacations with his former fiancée to Grand Cayman, which is a place now and forever tainted by those painful associations. It inspired a song called “I Can’t Go There” from the 2002 album No Shoes, No Shirt, No Problems. And it was his quest for a fresh place in the sun that brought him to St. John in the U.S. Virgins.

“I was running from insecurities and a love affair,” he says, “and chasing something — peace or resolve. And one reason I fit in on St. John is that I saw a lot of commonality. There are a lot of people down there in the same boat, emotionally.” 

Same boat, perhaps, but they probably don’t commute to the islands by Lear jet. The folks who populate Chesney’s Caribbean songs include dropouts living off the tourist trade, like the harborside shopgirl from “Boston” and the bartending subject of “Sherry’s Living in Paradise.”

Chesney first visited St. John with his father for a brief vacation, then took his whole band down for a month, making friends with the people who, he says, showed him a different way to live. “There’s beaches all over the Caribbean,” he says, “but the people there made me feel at home, made me feel like a local.”

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