Sailing employs the wind—acting on sails, wingsails or kites—to propel a craft on the surface of the water (sailing ship, sailboat, raft, windsurfer, or kitesurfer), on ice (iceboat) or on land (land yacht) over a chosen course, which is often part of a larger plan of navigation.

Cross has said in interviews that the song's inspiration was his friendship with an older friend from his high school, Al Glasscock, who would take him sailing as a teenager, just to get away from the trials and tribulations of being a teenager.