Cross wrote this song about his memories sailing every summer with a friend in Texas. ... On the Howard Stern radio show, Cross explained that sailing with his friend got him away from the trials and tribulations of being a teenager.

Did Christopher Cross actually sail?

That night he would take home five Grammys in total. Three of the awards that night were for his introspective hit, "Sailing," which (according to Cross) isn't actually about sailing. "I picked sailing as a metaphor because I used to do some sailing with an older kind of 'Big Brother' person in my life," he said.

What is with Christopher Cross and flamingos?

Flamingo. One common feature of Cross's album covers is the appearance of a flamingo. According to Cross, there is no meaning behind this, other than that the painting chosen for the first album cover featured the bird, which has been used as a motif ever since.