Kenny has traveled the world and performed alongside artists like Dave Matthews. He even sang for President George W. Bush at the White House. But he still has a few dreams left for himself and his family.

With Oprah Show cameras in tow, Kenny heads to Tennessee to check one item off his list. Even though Kenny owns a private jet, his grandmother, Lucy Grigsby, has never flown in an airplane. "That's about to change," he says. "We are going to go to Florida Keys, and we're going to go to my favorite restaurant [Blue Heaven], eat some key lime pie and have some fun."

Kenny hops in his SUV and drives to his grandma's house to pick her up. "Coming home is always a welcome break," he says. "I love that I can walk in here and just be 12 years old again."

Despite some preflight jitters, Lucy climbs aboard Kenny's plane and buckles up. "I didn't think I'd ever do this," she says. "I just always thought I'd be afraid."

Watch Kenny and his grandma take flight. Watch

After an unforgettable day of sunshine, sand and key lime pie, Kenny and his family head back to Tennessee. "I'm getting as much out of it as she is, I promise you," he says. "Being with my grandmother feeds my soul."

Music will always be part of Kenny's life, but he says the new dream he has for himself is to get married and have children.

"I'm always going to want to write songs and get out and play them for somebody," he says. "But, yes, I could see me settling [down] at some point."

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Watch as Kenny surprises one of his biggest fans. Watch


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