As with all of Newman's early albums, several of its songs had been previously recorded by other artists. In this case, "Simon Smith and the Amazing Dancing Bear" had been a UK hit for Alan Price in 1967, and "Dayton, Ohio - 1903" had been recorded by Billy J Kramer as a single in 1969 and by Harry Nilsson on his 1970 album Nilsson Sings Newman. Newman himself had also previously recorded "Last Night I Had A Dream" as a single, issued in September 1968. The version heard on Sail Away is a re-recording with a notably different arrangement.
"He Gives Us All His Love" was also initially written and recorded by Newman in a sparser and slower arrangement for the 1971 film Cold Turkey. The film issued no soundtrack, and the first commercially available recordings of this song were issued by Sundance (March 1971) and Ed Ames (October 1971).
The song "Lonely at the Top" was written specifically with Frank Sinatra in mind, although he never recorded it.