The Peaceful Meaning Behind “Sailing” by Christopher Cross

When life gets hard, “Sailing” could be the tune to deliver some peace. When Christopher Cross was a teenager a friend would take him out on a boat to get away from everyone else, Cross revealed during an episode of The Howard Stern Show. The meaning behind the hit track is about finding solace as it relates directly to the songwriter’s literal experience with sailing.

In the song, sailing can be understood as a metaphor for finding an activity that clears a person’s mind. There is another line in the song, which refers to painting: The canvas can do miracles. According to Cross, the song’s lyrics also speak about the transformative power of art.

It’s not far to never never land
No reason to pretend
And if the wind is right you can find the joy
Of innocence again
Oh, the canvas can do miracles
Just you wait and see, believe me
Sailing
Takes me away to where I’ve always heard it could be
Just a dream and the wind to carry me
Soon I will be free

A bridge for a troubled writer

When Cross wrote the song, the music and words came easily at first. “It’s one of these mystical things,” he explained in an interview with Rick Beato. “I was just messing around the kitchen table and believe it or not, I played basically the structure of the song.” The words flowed out of Cross and he wrote them down, surprised by how “pretty” they were. He was missing a bridge though and it took over a year until he found something that stuck.

The reason why it took so long was the way he had tuned his guitar, Cross shared, telling Beato that he listened to Joni Mitchell a lot over the years, becoming a “massive fan”, and admiring her approach to playing guitar. As a result, he often had his guitar in an open tuning. On the day he wrote “Sailing”, it was in an open D tuning when he picked it up. “You can get trapped where it’s almost like a mantra,” he explained of his dilemma. Different guitar tunings alter the harmonies a player has at their disposal. Finding the bridge that would “lift” the song out of the linear harmony of the verse and chorus, was not an easy task.

The patience paid off. In 1980, Cross won five Grammy awards, including a sweep of the General Four categories (Album, Record, Song Of The Year, and Best New Artist). The singer/songwriter from Texas also performed “Sailing” during the ceremony. According to the Recording Academy, Cross is the only artist in GRAMMY history to win all the General Four categories in one night.

A timeless song

In recent years, Cross needed the song as much as anyone else. In 2020, the singer was supposed to go on a national tour and celebrate the 20th anniversary of his self-titled debut album, which features the No. 1 Billboard hit “Sailing,” but instead of playing his music on stages all across the US, Cross first got sick with COVID and shortly after found himself suddenly paralyzed. He was unable to walk, let alone play the guitar. 

“It was certainly the darkest of times for me,” he said in an interview with CBS. His doctor diagnosed him with Guillain-Barré Syndrome and Cross had to be admitted to an intensive care unit, not sure whether he would survive. 

But these days, he is performing “Sailing” again, alongside other Top 20 Billboard songs from his debut album—”Ride Like The Wind” (No. 2), “Never Be The Same” (No. 15), “Say You’ll Be Mine” (No. 20). After ten days in the hospital and a long recovery, Cross is able to walk and play the guitar again. He told CBS he considers himself a long-haul COVID survivor.

Photo by Chris Walter/WireImage