WhenCharles Kelleywas growing up in Augusta, Georgia, he spent two summers working on his dad’s farm in the North Georgia mountains, raising cattle and riding around on a tractor day-in and day-out.

As a kid, theLady Antebellumsinger never thought he’d travel outside of America’s borders. One year atThanksgiving, which Kelley said was a meal with about 75 people in his household, one of his cousins was talking about a trip he’d taken toChina.

“I remember going, ‘Man, you’re crazy dude,'” Kelley, 36, tells PEOPLE in this week’s issue, on newsstands Friday. “I’m never leaving Georgia.America’s the best.”

Andrew Southam

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Cassie, Ward and Charles Kelley photographed for PEOPLE in Alys Beach, Florida on Aug. 6

However, once the musician joined Lady Antebellum and began touring and vacationing with his family, he gained a different perspective and admits that down the road, he’d love to retire somewhere like Positano, Italy.

“I had never really seen the world until Lady Antebellum,” Kelley says. “You can have pride in your country, but when you get to go and travel and see all these different places, it’s so eye-opening. There’s so many different ways of living.”

The singer has now circled the globe sharing his music with fans, and often brings his wife Cassie and son Ward Charles, 2½,on tour with him. He believes that so far, Ward has been on over 100 flights, and has visited multiple continents, including Europe.

Although Kelley wants to give his son the experiences he didn’t have growing up, he also admits that bringing him out on the road is “selfishly” so he can watch him grow up. The singer and Cassie, 35, were open about their previous fertility struggles before welcoming Ward — “it really did feel like kind of a miracle,” he says. “And I don’t want to miss a thing.”

Kelley adds, “My wife and I have such a strong relationship that it’s just so much better when they’re out with me. Having them with me is so cozy. I also don’t want Ward to grow up [and] be like, ‘I never got to see my dad — he was always traveling.'”

The"You Look Good" singersays his son is in a phase of copying everything Dad does, and because Kelley is an avid golfer, he bought Ward a tiny set of clubs to accompany him on the course. For the Kelley family, their “happy place” is often one of their favorite beach destinations — they have a home in Florida — but they also enjoy parks and zoos.

“He’s got such a unique situation to be able to see the world that most kids don’t have,” Kelley admits.

“I want him to grow up knowing how privileged he is and to not take it for granted. We’ve brought him along and really wanted him to be a part of our lives — not just this kid that you see every once in a blue moon. I want him to be proud of what I’m doing and hope I’m a good example for him.”

Catch Lady Antebellumon the road this summerwithDarius RuckerandRussell Dickersonon theirSummer Plays on Tour.

For more with Charles Kelley, Thomas Rhett and other country dads, pick up the latest issue of PEOPLE, on newsstands Friday.

source: people.com