It is the follow-up to his 1959 debut Lance Hayward at the Half Moon Hotel and is the second-ever album released on Chris Blackwell's Island Records.

Lance Hayward had performed in Jamaica during the winters of 1957-58 and 1958–59, and during the 1959–60 season was hired to lead the house band at the Half Moon Hotel in Montego Bay.

According to the album's liner notes, the selections are "the most requested numbers in the Hayward repertoire, during their winter engagement at Half Moon," which suggests the recording was done in the spring of 1960.

"Old Devil Moon" features Jamaican singer Totlyn Jackson, who joined the group for its summer 1960 residency at the New Windsor Hotel in Hamilton, Bermuda.

The cover photograph of the band at Sunset Beach, Montego Bay was taken by Horst Ebensberg.