Kenny Chesney Takes Entire Crew on Tropical Vacation

It’d sure be nice to work for the king of touring. Kenny Chesney treats his entire staff and crew each year on a vacation on his dime, Taste of Country reports. Doesn’t he seem like the kind of boss we all want to have? He takes care of his crew, and I mean he takes care of his crew: every night they all put their names in a hat and the winning name gets to take home what the merch tent makes that night. Once, that total was over $300,000 for a lucky staff member. Wow!

“I want to know about their family. I want to know what they do in their down time. I want to know what their dreams are. I want to know what they watch on TV. I don’t care about their religion or their political views. I don’t care about any of that.”

Every year since 2002, Kenny takes his crew and their girlfriends and wives on a trip to the Virgin Islands – and he pays for the entire thing!

What country artist would you love to work for?

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A 26 year-old Canadian girl currently living in England for a culinary career. Fell in love with country music and cooking at a young age, and looks for a way to do both.