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In the late seventeenth century, Captain Kidd and his pirates dock on the island of Tortuga for some recreation. Meanwhile, Rocky Stonebridge and Oliver "Puddin' Head" Johnson, who are working as tavern waiters for their passage back to America, are asked to deliver a love letter from Lady Jane to the tavern's singer, Bruce Martingale. Before they can deliver the letter, Puddin' is sent to wait on Kidd, who is dining with his rival, the beautiful Capt. Bonney. Accusing Kidd of pillaging in her "territory," Bonney demands that stolen jewels be turned over to her. When Kidd claims they are buried on Skull Island and shows her a treasure map, she decides to accompany him there on his ship, with her own ship following, in case of trouble. Their discussion is interrupted by Puddin's bungling entrance with the food, and during the resulting disorder, the treasure map and Jane's love letter are inadvertently switched. When Rocky and Puddin' discover the mix-up, Rocky realizes the importance of the map. They try to trick Kidd into taking them to the island by disguising Puddin' as an important naval officer, but the disguise is discovered. To save Puddin' from Kidd's wrath, Rocky tells him they have hidden the map, and then negotiates for Kidd to take them to the island and share the wealth. As Rocky and Puddin' return to the ship with Kidd's first mate Morgan and the other pirates, Puddin' tosses what he thinks is the love letter to Bruce, who, wondering why his friends gave him a map, follows them to ask, and is shanghaied. On the ship, Kidd searches Puddin' and Rocky for the map, planning to feed them to the sharks afterward, but finding only the love letter, he puts them in irons. Enticed by the love letter she thinks Puddin' wrote, Bonney frees them, in return for the map, but discovers later that they gave her the love letter. When an English merchant ship, in which Jane is a passenger, approaches, a sea battle commences, and Jane is captured. In exchange for Jane's life, Oliver gives Kidd the map. Later Puddin' stumbles into Bonney's room and discovers that her ardor for him is getting hotter. However, Rocky pulls Puddin' away to search the captain's room for the map, which Puddin' memorizes, then eats, just before Kidd catches him. At the sight of Skull Island, they all disembark and row out to search. Ordered to lead them to the treasure, Puddin' finds a spot and begins digging, while Jane and Bruce find a spot to continue their courting. After several hours, Puddin' uncovers a chest filled with jewels, but Kidd, who feels obligated to remain true to his reputation, announces his plans to double-cross all of them. Knowing she is to be killed later that evening, Bonney saves Puddin' and Rocky from a live burial and proposes a means of escape. That evening, according to Bonney's plan, Jane and Bruce distract the pirates, while Bonney signals to her ship. Puddin' knocks out Kidd and steals his clothes, then posing as Kidd, rescues Jane from the pirates. Bonney's men then fire their cannon at Kidd's men, while Bonney and the rest of her new cohorts prepare to carry the treasure by boat to the ship. In his disguise, Puddin' is mistaken by Bonney's men for Kidd and fired upon, but he survives. Kidd, Morgan, Rocky and Puddin' lead each other on a merry chase, but eventually Kidd is captured and hung by his feet on the ship's yardarm and Morgan volunteers to become a loyal second mate. After Puddin' and Bonney share a noisy and passionate kiss, Puddin' takes over as skipper and they all sail away.