Songfacts®:

• This stripped-down number is a tribute to some of the free spirits Kenny Chesney has met during his travels around the Caribbean, Mexico and Key West, Florida. "Every one of the guys in this song, every one of the people I've met in the islands, Key West, Mexico and even on the road, they're all very different - except how much they love the water or the road," said Chesney. "Those things take them away, bring them back, but mostly allow them to be free. This song feels like it distills their soul into a just a few lines."
• Chesney is an Ernest Hemingway fan, and he sees in the song some of the characters that Hemingway created in his novels. "That whole idea of this man who's lived his life on the water, and what sailing means, how they share it with others," the singer reflected.
  
  "It was the first thing I thought when I heard it," he added, "and it really lifts up those guys who have so much swagger, but no real need to let you know."
• Described as a mix of a "shanty" and a "lullaby," the song features Jimmy Buffett collaborator Mac McAnally on acoustic guitar and Vince Gill's keyboard player John Hobbs on piano.