Brantley Gilbert will headline one night of the Tropical Nights Boots in the Sand getaway next year at Mexico's opulent Riviera Maya resort. The singer says the trip will be his second to the country, and that his return will be bittersweet.

"I went for Christmas last year," he recalls to Taste of Country. "I can’t really say a whole lot about that story because, you know, I was there with my ex-fiancee [Jana Kramer]. But what I loved about Cancun is it’s like an extension of America and you can use your debit card to get Mexican money at the debit machines. So that saved my ass over there."

The 'More Than Miles' singer, who became sober in 2011, says that he apparently had a few other trips to beach locales, but he doesn't remember any of them.

"My police record says I went to Panama City, but I don’t recall it. My arrest report says I’ve been to Panama City a few times," he admits. "I was a wild one back in them days. A lot of my buddies know the story better than I do."

The singer, who is booked to do a stand-up paddle board excursion while in Mexico, says the thought already terrifies him. "I’m not real good at surfing, and I’m terrified of sharks," he concedes. "That’s like one of my main fears. Snakes, sharks, deep water and commitment. I think those are my four big ones."

But while the 28-year-old insists he will conquer at least some of his fears that day, he says doing thrill-seeking activities without alcohol poses a different challenge for him.

"When I drank, I would try just about anything," he explains. "If it would make anybody laugh or was something we could get on camera and it would be a miracle if it actually worked, then I was all over it."

Gilbert and Kramer will headline separate nights of the upcoming event, along with Dierks Bentley and Billy Currington. He is also putting the finishing touches on his new album, which should be available early next year.