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Florida socialite Ann Andrews becomes infatuated with a Caribbean nightclub singer, Juan Matanza, whom she has only seen in a photograph. In order to meet the singer, she convinces her father to allow her to take a Caribbean holiday with four girl friends and a spinster chaperone. Before leaving, Ann's guide relinquishes his job due to an intense fear of flying, and asks Harry Bernard, a virtual stranger, to take over for him. This fits in with Harry's plans, as he is trying to elude Joe and Wilbur, New York detectives who have followed him from the city. While flying to the islands, Ann attracts the attention of pilot Don Terry, who asks her out to a nightclub when they land. As she plans to search the nightclubs for her photograph lover, Ann agrees. When she then learns that her dream lover sings at a club on the island of La Monica, she convinces Harry to take her and her friends there, inadvertently providing Harry with yet another escape from the detectives. The entire island of La Monica is celebrating a carnival, and Ann and her pals go to see her singer and discover that he is unattractively overweight and years older than his picture would suggest. Ann realizes that she is really in love with Don and goes to him, while Harry learns that Joe is merely bringing him news that he has won a lottery.