The Simpsons are going to Italy...to help Mr. Burns retrieve his sports car, and end up in an Italian village where Sideshow Bob is now married with a son.

!! Tropes:
* AllPartOfTheShow: When Bob's family disguise themselves as extras to kill the Simpsons in the Colosseum, Lisa tells the audience that it's no act and that they're really trying to kill them. Nobody is convinced.
* ArtisticLicense: {{Cars}}: Driving a car over an aquaduct is pretty impossible.
* UsefulNotes/BenitoMussolini: Lisa scolds Homer for imitating Mussolini on the balcony. He claims he's imitating DonaldTrump, though.
* BlessedAreTheCheeseMakers: Subverted when the Simpsons' car is hit by several Italian cheeses.
* ComicallyMissingThePoint:
-->'''Lisa:''': "Dad, you're driving on an ancient Roman aquaduct."
-->'''Homer:''': "What am I supposed to use it for? Transporting water to distant urban centers?! Lazy Romans."
* ElNinoIsSpanishForTheNino: When Bob swears a vendetta on the family, Marge looks in an Italian-American dictionary and is shocked that "vendetta" means "vendetta" in English.
* TheFamilyThatSlaysTogether: Provides the page image.
-->'''Bob:''' Revenge is a dish best served...''family style''.
* GladiatorGames: While in the Colosseum Bart shows his historical ignorance by saying: "Oh no! We're going to be the first Christians to die in the Colosseum!"
* GoodBadTranslation: "Plagiarismo" is not the correct Italian word for "plagiarism". It's "plagio".
** Krusty makes a joke about "a wife showing him her "Naples". The joke falls flat because one Italian correctly remarks: "We call it "Napoli".
* HistoricalInjoke:
--> '''Homer''': "Stupid Italy. Wish you'd never been unified by Victor Emmanuel II. If only you'd stayed a loose confederation of city-states, trading with each other and occasionally warring."
--> '''Bart''': "Please help us, Krusty. We don't want to be the first Christians to die at the Colosseum."
* IgnorantOfTheirOwnIgnorance:
** '''Marge''':"Bart, Bob is a family man now. You can't be a bad person if you have a family."
* LoopholeAbuse: Mr. Burns had Homer bring his new car from Italy to save tax money.
* TheMafia: Referred to only once, according to an old village lady their small village is run by the Mafia.
* MyCountryTisOfTheeThatISting:
--> '''Bart''': "What's with the Canadian flag on your backpack?"
--> '''Lisa''': "Well, some people in Europe have the impression that America has made some stupid choices in the past, oh, five years. So, for the next week, I'm from Canada."
--> '''Bart''': "I think dad may blow your cover."
--> '''Homer''' (battling over a flag): "That flag is mine! Don't mess with Texas! Shock and awe, losers! Shock and awe!"
* NationalStereotypes: Several references to Italy are made, including stylish cars, spaghetti, the Leaning Tower of Pisa, Pompeļi, the Pontevecchio Bridge, Creator/FedericoFellini, Italian cheese, chianti, Toscany, TheMafia, vendetta, olive gardens, aquaducts, the Colosseum, opera and Venice.
** Bart makes a tiny reference to Literature/{{Pinocchio}} too, after watching a horrible educational video at the start of the episode: "What is this crap? This is worse than "Wheelchair-nocchio."
* OliveGarden: Can be seen in the village.
* {{Opera}}: The final scene takes place at an opera.
* ShoutOut: The song Sideshow Bob sings while squashing grapes with his feet is a reference to Nancy Sinatra's song "These Boots Are Made For Walkin'".
* Theatre/{{Pagliacci}}: Sideshow Bob disguises himself as Pagliacci, and gives a far better performance than Krusty did.
* TakeThat: According to an Italian police book, [[WesternAnimation/FamilyGuy Peter Griffin]] is wanted for plagiarism and [[WesternAnimation/AmericanDad Stan Smith]] for plagiarism of plagiarism.
* TranslationByVolume: The elderly woman Homer approaches doesn't know any English, so he decides to shout out all of the details of the Lamborgotti Fasterossa in her face.
* VacationEpisode: The Simpsons travel to Italy.
* WhoWritesThisCrap: Krusty says this when his opera act starts to go south.