Brett James told Roughstock
how he and Chesney penned the song during a last minute writing trip. "Kenny called me on Christmas Eve a couple of years ago," he recalled. "I was standing in my kitchen, and he goes, 'Hey man ... what are you doing the day after tomorrow?' I was like I have a wife and four kids ... it's Christmas vacation. I said, 'Nothing. What do you have in mind?' He was like, 'I'm going down to the islands to write some songs.' That sounded like more fun than what I had planned. Forty-eight hours later, Kenny and I were on the islands.
"Like most people probably do in the islands, the first night you're there, you're all excited, so we went out and had fun," James continued while smiling. "He did get in much later than I did, for the record [laughs]. The next morning, I was on his balcony. He's got one of the prettiest balconies I've ever seen. I was strumming on my guitar. He walked out and kind of wiped the sleep out of his eyes, and he said, 'Man ... we went out last night! I was like, 'Hey! That's our title'.
"We just started writing right then," added James. "All I remember about writing that song is laughing. We had a ball writing that song. The fun thing about that song, too, is that we wrote that song around his pool, then later that afternoon, we wrote 'Reality
' by the pool. Thanks to Kenny Chesney, I had a day where I got to write two #1 songs in a day. That will probably never happen again in my life [laughs]! Thank you, Kenny ... where ever you are!"