Homer is suffering from insomnia due to stress about his age. In an attempt to heal, the family takes a vacation to Florida. Little do they know, it is spring break when they arrive. After Homer accidentally "kills" the town alligator mascot, the family must go into hiding to avoid getting arrested.
Homer gets a magazine in the mail that is loaded with personality tests and he relentlessly quizzes his friends and family with them. Later on he takes his own test, which determines how long he has left to live. Unfortunately, Homer is less than stellar health and eating habits add up to only three more years to live. Marge suggests a few lifestyle changes to make that number go up. Naturally, Homer is against that and has a mental breakdown, developing insomnia and losing his sanity. He almost causes the Power Plant to be closed down when he asks the safety inspector to hide him, wearing nothing but a burlap sack and holding a toy baby. The plant's counselor recommends Homer go on a long vacation for quiet recuperation, so the family head off to a town in Florida. Unfortunately, when they arrive it is Spring Break, one of the loudest weeks of the year. Although Homer is cured of his death paranoia, he now has a new problem: running off to a Kid Rock concert on the beach when he should be resting. Homer becomes a nuisance at the party, annoying the audience, Joe C. and Kid Rock. Homer wakes up the next day, with his insomnia gone, he rushes outside ready to party but spring break is over: The students are returning back to their studies.
Homer tries to keep the party going, dragging the family along with him. He rents an airboat and they go through the swamp, while Homer is having fun, the kids are not enthusiastic. While riding Homer ends up running over the town's most famous resident, an alligator named Captain Jack. Despite the fact that Homer is the sole guilty culprit, the entire family is arrested for killing the alligator. They flee from the Sheriff and head for a railroad crossing just as a freight train is going by. Although Homer is able to dodge the train, their car is hit by an Amtrak train traveling in the opposite direction and pushed several miles down the tracks. The Simpsons go to a secluded diner, and work there until the heat is off. They soon begin to enjoy their life in Florida and Homer even says, "Killing that Gator was the best thing that could have happened to us!" and the whole family agrees. The family is soon tracked down and taken into custody by the sheriff. The family is sentenced to life imprisonment as well as forced labor. One night they attempt to escape but ultimately fail. However, before the family can be arrested again, Captain Jack appears - He wasn’t dead at all, he had only been stunned by the boat's impact. The family is acquitted but they are banned from entering Florida again. For their next trip, the family plans to go to North Dakota or Arizona as those are the only other states they are allowed in. They decide to finish off their trip in North Dakota since Homer complains that Arizona "smells funny".
Behind the Laughter
This episode was met with universally negative reception due to the plot of the main episode, and the Simpsons getting arrested multiple times and then banned in nearly all states. It is often cited as one of the worst episodes of the show. In 2006, Nohomers.net named this the worst episode in the history of the show. Some fans have asked for the events of this episode to be rendered non-canon.