Click for larger image

When his cruise ship, the Cuban Queen, runs aground near Florida on its way to Havana, New York ocean liner magnate Walter McCracken sends his vice-president, Jay Williams, to the site to forestall any legal action.  Jay gets the passengers to sign claim waivers in exchange for future passage on another McCracken ocean liner.  One passenger, Macy's salesclerk Nan Spencer, refuses to sign, because she has saved for years for the vacation and cannot take it at any other time.

When Nan hints that she is aware of the captain's negligence in the accident, Jay accedes to her demand that the company ensure her an enjoyable vacation in Havana.  Nan refuses to sign the waiver until after her vacation is completed, so McCracken orders Jay to accompany her, even though he is soon to be married to McCracken's snobbish daughter Terry.

Upon reaching Havana, Nan is delighted with the scenery but bored with Jay, who is too stodgy to provide the romance she craves.  When charming fortune hunter Monte Blanca comes across Nan, he believes that she will be the solution to his gambling debts.  Monte takes Nan to a casino run by Boris, who threatens Monte upon discovering that Nan is a simple salesclerk who cannot make good on the losses she believed Monte himself was going to pay.

Jay, who has followed the couple, offers to pay off Monte's debts if he will romance Nan, thereby making sure she has a good time and will sign the waiver.  Monte readily agrees, despite the jealousy of his tempestuous girl friend, Rosita Rivas, a singer whom Monte manages.  In order to forestall Rosita's tantrums, Jay agrees to be her new manager, but regrets his decision when it becomes apparent that she wants romance as well as advice.

One evening, Rosita meets Jay at a secluded inn, but Monte and Nan are already there, and during an ensuing argument, Monte reveals that he accepted Jay's proposition in order to repay Rosita money he owes her.  Nan is furious at both men for the deception, and when Jay tries to follow her after she leaves, his car is accidentally wrecked.

While walking back to town, Jay and Nan discover that they are genuinely attracted to each other.  The next morning, happy that her vacation is going well, Nan gives Jay a signed waiver, but tears it up when Terry appears and intimates that Jay's behavior has been strictly business.  Heartbroken, Nan signs another waiver and accepts from Terry a check for $1,000, which Terry says came from Jay.  When Jay sends her a check for $150, however, Nan realizes that Terry was trying to bribe her without Jay's knowledge.

Terry's scheming soon becomes apparent to Jay as well, and after he angrily sends her back to New York, he finds Nan in the nightclub where Rosita is performing.  As Rosita and Monte dance together, Jay and Nan are reconciled, and everyone sings the praises of their weekend in Havana.

Notes
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 HR news item also noted that Grable and Fonda were set for the lead roles, while a May 2, 1941 HR news item stated that Don Ameche would have a lead role.  HR 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 HR 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.  HR 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 HR 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 HR 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.

Music includes:  "A Week-End in Havana," "When I Love, I Love," "The Man with the Lollypop Song" and "The Nango," music and lyrics by Mack Gordon and Harry Warren; "Tropical Magic," music and lyrics by Mack Gordon and Harry Warren, Spanish lyrics by Ernesto Piedra; "Rebola Bola (Embolada)," music and lyrics by Aloysio Oliveira, Nestor Amaral and Francisco Eugenio Brant Horta; "Romance and Rhumba," music by James V. Monaco, lyrics by Mack Gordon.