[1] Recorded in 1942, the song was released as a Victor 78 single by Glenn Miller and His Orchestra in 1943 as the B side to "Blue Rain".

The title is a reference to the Pan American Airways Caribbean Clipper, which was one of the first commercial airliners to fly regularly scheduled transatlantic routes.

Mel Powell played piano on performances with the Glenn Miller Army Air Force Band.

[14][15] The personnel for Miller's 1944 Abbey Road recording were:[16] A number of strings musicians were part of the ensemble,[16] but the song's orchestration did not require their performance.

The song was performed by the BBC Big Band as part of their Glenn Miller tribute concert at Birmingham Town Hall on November 14, 2011.