Published in 1935, its music was written by Hugh Williams (pseudonym for Wilhelm Grosz) with lyrics by prolific songwriter Jimmy Kennedy. The song was inspired by the "red sails" of Kitty of Coleraine, a yacht Kennedy often saw off the northern coast of Ireland and by his adopted town Portstewart, a seaside resort in County Londonderry.
The title of the song provides the inspiration for the Red Sails Festival held annually in Portstewart, Northern Ireland. Kennedy wrote the song while staying in Portstewart.
Some of the earliest versions were recorded by Al Bowlly with Ray Noble and his Orchestra on September 18, 1935 and Guy Lombardo, on October 11, 1935. This recording was issued by Decca Records as catalog number 585.
The song was revived by Nat King Cole in 1951. This version was released by Capitol Records as catalog number 1468. It first reached the Billboard magazine Best Seller chart on July 13, 1951 and lasted 2 weeks on the chart, peaking at #24. Another version was released in 1954 on MGM 11977 by Sam "The Man" Taylor on and His Orchestra, with Sam on tenor saxophone.
An instrumental version of the song became the signature tune of the Philippine radio drama series Dear Kuya Cesar, broadcast on DZMM radio (ABS-CBN) in the sixties and hosted by Cesar Lacbu Nucum, a.k.a. Kuya Cesar. The song was also the signature tune of Suzette Tarri, a British actress and comedian popular on stage and radio in the 1930s and 1940s.
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