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.