Homer reacts with great enthusiasm when his first issue of Self-Test Monthly arrives in the mail. After donning robes and an orange highway cone for a hat, Homer sets about quizzing friends and family alike. But when he answers a self-quiz that claims to predict a person’s longevity, he is shocked to learn that, according to the quiz, he has only four more years to live.

The news chips away at Homer’s sanity, and he begins hallucinating while watching Charlie Rose interview legendary producer Robert Evans on television.His mental condition deteriorates further when he hops around the nuclear power plant in a sleeping bag with cowboy designs.Mr.Burns notices the strange behavior,and soon after,a psychiatrist examines Homer.The psychiatrist tells Homer to take a long vacation in Florida.

Soon after, the Simpsons embark on a trip to the Sunshine State…only to realize Spring Break is in full swing. Soon after, Homer assists a bunch of partying college students as they roll the Simpsons’car upside-down (with Marge still inside). Marge ties Homer to a bed in their hotel room and sets off with the children for some sightseeing.

But despite being strapped to the bed, Homer manages to extricate himself from the hotel room and bum a ride with a van full of college kids. Homer eventually ends up on the beach, where an MTV-like stage is set up on the sand, complete with elevated dance platforms. VJ introduces singer Kid Rock, who launches into Bawitdaba. Unfortunately, Homer gets drunk and angers the crowd of rockers, who threaten him with a flaming amplifier. Luckily, the local sheriff s teps in and saves Homer from harm.

Meanwhile, Marge and the children tour a Florida swamp in an airboat, where a tour guide points out a legendary alligator named Captain Jack, who is revered by citizens far and wide for helping build the town of Palm Corners. When Marge and the children return to the hotel, Homer is not to be found. The sheriff, however, escorts Homer back to the room.

Soon after, Spring Break ends and all the college students leave town. Unwilling to accept the lack of a party atmosphere, Homer rents an airboat and takes his family for a ride in a swamp. While touring the area, Homer accidentally runs over Captain Jack the alligator. The sheriff suddenly appears and arrests the family for killing the beloved creature. But thanks to Homer’s quick thinking, he and his family manage to escape in their car. The sheriff pursues them…until the Simpsons’ car is broadsided by a train, which pushes the car for miles down the tracks.

When the Simpsons awake the next morning, the train is still pushing the car down the railroad track. Eventually, a young trainman pries the car loose, causing it to tumble down an incline. The Simpsons make their way to a run-down country diner, where the owner, an old country woman, hires them.

Soon after, the family adjusts to country life, having taken up residence in a nearby run-down trailer. But one night, the sheriff hitches the trailer to his police car and drags the family off to jail. The judge sentences the Simpsons to a year on a chain gang. Eventually, however, the family ends up helping the judge with a soiree at the courthouse.

The Simpsons make another escape attempt, but it is soon thwarted. Just as the sheriff sentences them to "the box," Captain Jack, whose body was laying in state at the courthouse, suddenly revives. The judge overturns the conviction and the Simpsons are set free.