The Simpson family attends the 65th Annual Springfield Pride Awards, hosted by Kent Brockman and singer Britney Spears. Homer eagerly anticipates being called to the stage, as he believes his numerous contributions to the city cannot go unrewarded. But despite his initial confidence, several other residents, including Krusty the Clown, are honored with an award.

One such honor is given to Cornelius Chapman, a one hundred and eight year old man and Springfield’s oldest resident. Unfortunately, Chapman dies moments after receiving the award. Undaunted, Brockman vows to hand out the award. It is eventually determined that the oldest living resident is none other than Mr. Burns, who is handed the award when he takes the stage.

Later, Burns decides his advanced age means taking better care of himself. When Smithers schedules a medical check-up for him at the Mayo Clinic in Minnesota, Burns decides to have Homer and his family housesit the mansion during his absence.

Homer and his family live the good life while Burns and Smithers are out of town: Lisa rides a Shetland pony through the house; Bart smokes one of the billionaire’s cigars; and Homer jimmies open his liquor cabinet and makes numerous long distance phone calls. Eventually, Marge demands that Homer stop acting like a billionaire, as Burns will be returning to the mansion the following day.

Instead, Homer decides to throw a party. But when he attempts to purchase four kegs of beer, Moe reminds him that state law prohibits the sale of alcohol on Sunday until 2:00 p.m. Unwilling to wait 45 minutes, Homer decides to pilot Mr. Burns’ yacht into international waters, thereby skirting the law. Despite protests from Marge,who fears the yacht will end up being ruined, Homer brings Lenny, Carl, Moe, Krusty, Apu and Chief Wiggum along for the journey.

Meanwhile, doctors at the Mayo clinic determine that Mr. Burns is the sickest man in the United States. But Burns, it turns out, has so many diseases that they create a perfect balance.

Later, as the yacht passes into international waters, many illegal items from other boats in the area, such as fireworks and fighting bulls, end up on deck. But unbeknownst to the revelers, pirates on a nearby ship observe their activities and take an interest in the many items on board.

The pirates board the yacht and hoist all of the party guests—save Homer—into the air using a large net. The pirate captain then instructs a subordinate to set sail for Hong Kong. Unwilling to climb into the net with his friends, Homer attempts to fight back. But his Erroll Flynn-like moves send him plummeting onto the deck in a heap. He then climbs into the ney. One of the pirates then cuts the rope holding the net, sending the group plummeting into the sea.

The net lands on a cruise ship, where Patty, Selma, Mrs. Skinner and other unmarried woman lie on deck chairs. Meanwhile, Marge and Lisa finish putting the finishing touches on their extensive cleaning work inside Burns’ mansion. Unfortunately, the obsessive Marge spots a tiny smudge on huge picture window overlooking the grounds, and when she tries to rub it off, ends up cracking the glass. Small cracks then extend outward in all directions.

Moments later, Mr. Burns and Smithers return from their trip. Marge and Lisa stand in front of the glass, attempting to block the damage. Suddenly, Bart and Homer, clad in Speedos, burst into the room. When Homer mentions Burns’ yacht, Burns bellows, "Release the hounds!" Smithers presses a button…but only the mournful yelp of a dog can be heard. Burns realizes no one remembered to feed his dogs. Sensing an opportunity, Lisa tells everyone to run