Esmerelda Fump is the ugly maid at the palace- but she finds that if she gets to sleep, she gets prettier and prettier. Seeing her in her "pretty" state, the prince wants to marry her, but she keeps having to go take a nap to avoid looking ugly. Finally, the prince calls the court wizard and asks him to make her into a "night owl"- which he does... literally!
The time travelers arrive in the palace of Cheops, the Second King of the Fourth Dynasty in 3,000 BC in Giza, on the border of the Libyan Desert. Cheops attempts different building feats in an attempt to outdo his rival--his five-year-old nephew, Prince Ahmed. Sherman and Peabody advise Cheops to build The Great Pyramid in order to show up Ahmed.
Sherman and Mr. Peabody travel to Cadiz, Spain in 1833 to watch a bullfight. Instead, they are treated to a bull...dog...fetching a stick. With the help of brave matador Porfirio, Sherman and Peabody overcome many obstacles in order to catch a real bull so that they may enjoy an authentic bullfight.
Peabody and Sherman travel to Toronto, Canada in 1869. They meet up with Constable Archibald Willy, who tries to capture Ottowa O'Toole, a woman who's on a wanted poster. Sherman and Peabody pose as Ottowa's two sisters, "Hermoine" and "Gingold," in hopes that the ruse will trap Ottowa. Instead, they are kidnapped by O'Toole but quickly rescued by Constable Willy.