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The working titles of this film were Caribbean Cruise and Honeymoon in Havana. According to the Twentieth Century-Fox Produced Scripts Collection at the UCLA Art-Special Collections Library, in early March 1941, Betty Grable was scheduled to play "Nan Spencer," and executive producer Darryl F. Zanuck suggested that Henry Fonda play "Jay Williams." A March 17, 1941 Hollywood Reporter news item also noted that Grable and Fonda were set for the lead roles, while a May 2, 1941 Hollywood Reporter news item stated that Don Ameche would have a lead role. Hollywood Reporter news items in late 1940 stated that Jack Andrews and George Seaton were to work on the film's screenplay. Although the extent of Seaton's contribution to the completed picture has not been confirmed, the Twentieth Century-Fox Records of the Legal Department, also at UCLA, indicate that Andrews' material was not used. The legal records also indicate that an original story outline entitled Caribbean Cruise, written by Frank S. Nugent, was not used.
The story files and Hollywood Reporter news items reveal that first Harry Joe Brown and then Fred Kohlmar were set to produce the picture. When Kohlmar left to work at Paramount, William LeBaron assumed production responsibilities. This was the first film produced by LeBaron for Twentieth Century-Fox. Hollywood Reporter news items reported that the studio had tested Phillip Reed for a role and were considering casting him in the picture, and that Mal St. Clair had been signed to direct the musical sequences. Their participation in the released picture has not been confirmed, however. According to studio records and Hollywood Reporter news items, "long shots with doubles, atmospheric shots and process plates" were filmed on location in Havana and the Cuban countryside. Second unit director James Havens and his crew were on location for approximately one month. A September 26, 1941 Hollywood Reporter news item announced that Alice Faye was going to retire from the screen temporarily while awaiting the birth of her first child. Faye returned from retirement in the 1943 Twentieth Century-Fox picture Hello Frisco, Hello.
According to information in the MPAA/PCA Collection at the AMPAS Library, the PCA rejected a May 14, 1941 version of the screenplay because of "the inference of an illicit sex relationship" between "Rosita" and "Monte," and "Jay" and "Nan," and the indication that "Rosita" wished to enter into such a relationship with "Jay." The PCA especially objected to the use of the words "manage" and "manager" in respect to the relationships between "Rosita," "Monte" and "Jay." In June 1941, the PCA informed the studio: "We still get the impression that the word 'manage' is so used, or over-used, that one gets the feeling that it is intended to mean something which is sex suggestive." The problems were eventually resolved and the script approved.