Songfacts®:

• Kenny Chesney owns a mansion on St. John in the US Virgin Islands. This song is a dreamy look at island life where the singer spends so much of his time. Over a simple guitar melody, he sings idyllically of being a pirate, imagining sailing on the seas, not tied down by the "9-5" responsibilities back home in the States.
  
  I wish I was a pirate out there under my own flag
  Running for no reason and no reason to turn back
  Salt and rum on my tongue, sails tattered and torn
  Laughing in the devil's face, riding out a storm
  
  "Anyone who's got a job, a schedule, a list of responsibilities and people to answer to understands that yearning to be free," Chesney said. "This song is about being unplugged, off the grid, sailing where the boat takes you and letting your cares drift away."
• Another Chesney song with a similar theme of a pirate living the free and easy life is his Life on a Rock track "Pirate Flag."
• In the early fall of 2017, St. John was devastated by Hurricane Irma. Some of the island's 4,500 residents stayed in Chesney's home to weather the storm; the singer has since done all he can to help his battered Caribbean friends. This song, along with many of the other Songs of the Saints tracks album focuses on the beauty of people coming together to recover.
  
  "'Pirate Song' emerged as a love song to everything the islands have always been: freedom, time slowing down, being calm and at sea," said Chesney. "Even when my friends and people I knew were coming through my house after the storms came through, I knew the essence of what those islands are couldn't be extinguished inside them."