Homer gets a magazine loaded with personality tests and quizzes his friends and family with them. Later on, he takes his own test which reveals that has only three years left to live. Terrified of his supposedly impending death, he develops insomnia and goes insane. Homer visits the Springfield Nuclear Power Plant's psychiatrist, who suggests that he take a long vacation. The Simpsons go on a trip to Florida and find themselves in the middle of a raucous spring break when they get there. Marge wants Homer to stay in his hotel room, but he escapes to party and attends a concert featuring Joe C. and Kid Rock. Homer becomes the life of spring break until it ends and the wild college students return to their studies.
Homer, who still wants to party, rents an airboat and forces his family to come with him. He races through a swamp, accidentally killing the state's most famous resident and reptile – an alligator named Captain Jack, whom Marge, Maggie, Lisa, and Bart saw on a tour earlier while Homer made a fool of himself at the concert. A sheriff quickly arrives on the scene and despite the fact that Homer is the sole guilty culprit, the entire family is charged for killing the alligator. The family members flee from the sheriff and during a car chase they are hit by a train that pushes their car on the rail for several miles. When the Simpsons get off of the rail, they escape to a restaurant where they are given employment. They live in a nearby trailer and progressively turn into hillbillies. The sheriff eventually tracks them down and kidnaps them while they are sleeping. For their crimes (and Homer's foolish attempt at defending himself in court), the family is put into forced labor. One night when they are working at a party held by a judge in front of the capitol, tending to the guests (and failing to escape), Captain Jack strolls out of the capitol's doors. It turns out that he was never dead but rather knocked out. The family is acquitted, though they are banned from entering the state of Florida again (and several other states, excluding Arizona and North Dakota).