Christopher Cross - Sailing "Sailing" is a 1979 soft rock song written and recorded by American singer-songwriter Christopher Cross. It was a hit in the United States, reaching number one on the Billboard Hot 100 chart on August 30, 1980, where it stayed for one week and peaked at number 6 on the Billboard Adult Contemporary chart. In Canada it was also a hit, reaching number one on both the RPM Top Singles and Adult Contemporary charts. | Music & Memories of the 50s, 60s & 70s