Mrs. Krabappel’s students moan in disappointment when their “special treat” turns out to be a multicultural PBS video produced by the National Film Board of Canada. A short time later the kids notice Mr. Burns outside the elementary school, standing next to his Stutz Bearcat, which has broken down. The kids mock Burns and his advanced age. As Smithers emerges from under the hood, he suggests to Mr. Burns that he consider buying a new car. At the nuclear plant Homer pounds his fist on a doughnut, causing jelly to squirt on a photo of Mr. Burns. Moments later Burns enters Homer’s work area and informs him that he purchased a Lamborgotti Fasterossa, an incredibly expensive automobile. Burns tells Homer he’s sending him to Italy to pick up the car from the factory. The Simpsons board an airplane and fly to Europe. Along the way Homer pulls some wires out of his armrest, causing an engine to drop off the plane. When the family arrives at the airport, Bart notices a Canadian flag on Lisa’s backpack. Lisa tells Bart that the United States has made some poor choices over the last five years, so she’s decided to pretend she’s Canadian. The family makes its way to the Lamborgotti factory, where they see Burns’ car come off the assembly line. A short time later they set off for Rome, where the car will be loaded onto a boat and shipped to Mr. Burns in Springfield. Along the way the family takes in the historic sights; including the Leaning Tower of Pisa, a Venice canal, and the ruins of Pompeii. Homer gets lost and accidentally steers the Lamborgotti into the path of a cheese truck. The truck jackknifes, causing cheese wheels to fly forward and flatten the Lamborgotti. Homer drives the damaged car to the nearby Tuscan town of Salsiccia, hoping to find a mechanic. Townspeople inform Homer that only the mayor speaks English. The mayor turns out to be Sideshow Bob. The Simpsons scream.

Sideshow Bob tells the family the story of how he ended up in Italy. After having once again failed to murder Bart, he decided he needed a new start in life, so he moved to the small Italian village. When the grape harvest began, the villagers marveled at the size of his enormous feet, which were perfect for crushing grapes. The following spring he was elected mayor. Sideshow Bob introduces the Simpsons to his bride, Francesca, and his son Gino. When Gino hears Bart’s name, he begins making stabbing motions, and repeats the phrase “Die, Bart” again and again. Sideshow Bob begs the family not to tell Francesca that he’s been in prison. Homer promises not to reveal the secret if Sideshow Bob arranges to fix the Lamborgotti. As the car is being fixed, the family tours the town, where Homer has a sausage maker grind some meat so it can fall directly into his mouth. Sideshow Bob throws the family a dinner to honor their return to America. During the meal Lisa drinks too much wine, and accidentally rips off Sideshow Bob’s shirt, exposing his prison jumpsuit. The crowd gasps. Francesca confronts Sideshow Bob about his past, and Bob is forced to admit he’s been to prison. He glowers at the Simpsons, who promptly jump into the Lamborgotti and speed out of town. Sideshow Bob swears a vendetta against them.

Riding a Ducati motorcycle, Sideshow Bob chases the family as they attempt to flee. Homer makes the mistake of turning the car into an aqueduct, and ends up stranding the vehicle on top of Trajan’s column. While walking through Rome, the family realizes Krusty the Clown is appearing in a local opera production. They burst into Krusty’s dressing room, where they beg Krusty for help. Krusty has them don costumes so they can appear onstage with him, where they will be safe from Sideshow Bob’s murderous rage. As the opera gets underway, Sideshow Bob replaces Krusty; and wearing Pagliacci costume and makeup, descends upon the Simpsons. He’s soon joined by Francesca and Gino, who assist him in carrying out the vendetta. Suddenly a limousine appears. Krusty opens the door and tells the Simpsons to climb in. Bart and his family thank Krusty for rescuing them. Krusty arranges to have the family and the Lamborgotti flown back to the United States.