Havana Wild Weekend is the seventh episode of Season 28.
When the Retirement Castle and the V.A. Hospital can't solve Grampa's health issues, the Simpsons plan to take a family trip to Cuba to get cheap medical care.
The Simpsons are watching TV when Homer observes a pee stain in the carpet. He immediately blames Santa's Little Helper, but to their surprise, Grampa confesses it was actually him. They realize that he is not so healthy, so they take Abe to the Retirement Home, but the best they can do is to dump him on Skid Row. They try taking Abe to a V.A. hospital, but his appointment is scheduled to twenty three years in the future.
Another veteran in the hospital sees Abe's situation and tell him that the best health care he can get is in Cuba, but even there the Doctor was unable to do anything. Abe was losing hope, to the point where he hugged Maggie goodbye, but while Abe is walking down the street, he admires a classic car. The owner offers Abe a ride which makes him feel much younger and able to enjoy Cuba a lot more.
At a bar, Abe meets a waitress who wants to hook with him later. He also encounters a friend from the army, who takes him to see a plane he hijacked. He plans on joining with Abe to make a party inside said plane. When Abe gets back to the hotel, he confronts Homer, saying that he wants to stay in Cuba.
Abe went to the party on the airplane with other war veterans, but Homer managed to track him down with the help of the U.S. Embassy. The bar's waitress seduces Abe into the cockpit, and reveals that she's a secret agent working for the CIA to take fugitives back to Miami. Back in the USA, Homer and Abe reconcile and plan to go to a golf course along with Bart to scare the golf players.