"Jamaica Farewell" is a mento about the beauties of the West Indian Islands. Mento is a style of Jamaican folk music that predates and has greatly influenced ska and reggae music. Mento typically features acoustic instruments, such as acoustic guitar, banjo, hand drums, and the rhumba box — a large mbira in the shape of a box that can be sat on while played. Harry Belafonte, a New Yorker of Jamaican origin, was one of many 1950s mento recording artists. His wildly popular hit records in 1956-1958, including "Day-O (The Banana Boat Song)" and "Jamaica Farewell," were mento songs sold as calypso. Previously recorded Jamaican versions of many Belafonte's classic "calypso" hits can be heard on the Jamaica - Mento 1951-1958 CD released by Frémeaux & Associés in 2009.

The lyrics for the song were written by Lord Burgess (Irving Burgie). Lord Burgess was born in Brooklyn, New York in 1926. His mother was from Barbados and his father was from Virginia. The song first appeared on Harry Belafonte's phenomenally successful album Calypso. It reached number fourteen on Billboard's Pop chart.

Though many, including Belafonte himself, have said that the song was popular in the West Indies since long before Burgess, it is believed that Burgess compiled and modified the song from many folk pieces to make a new song, and it is clear that it was Belafonte who popularised the song outside the Caribbean Islands. Burgess acknowledged his use of the tune of another mento, "Iron Bar".