Advertising agent Tony Marvin (Bing Crosby) devises a campaign for Todhunter's Imperial Pineapples in Hawaii to select a "Pineapple Girl" to find romance in Hawaii for three weeks, and later relate her adventures in print. When Georgia Smith (Shirley Ross) is selected but fails to find romance, Tony is pressured into providing it. Unknown to him, Todhunter also arranges for Tony and Georgia to receive a mysterious black pearl, which will lead them to an adventure on a smaller island.