When Grampa accidentally urinates on the carpet, the Simpsons try to get him medical help but find the nursing home has no resources or personnel at all, and the Veterans Administration tells Abe they can't see him for an appointment for 23 years. On the advice of another elderly ex-soldier, the family goes to Havana, Cuba to get Grampa cheap medical care. As they arrive there a friendly doctor sadly says there is nothing that can be done to help Abe, but the sights of cars and music from the 1950s leads to him feeling much healthier. While the family enjoys the sights of Havana, including Homer making a drinking game out of old speeches by Fidel Castro, Grampa meets a bar matron, Isabella, whom he fancies. He also runs into an old friend of his, a pilot who was thrown out of the Air Force for nearly detonating an atomic bomb by accident and stayed in Cuba after hijacking a plane and diverting it to there in the 1970s. He brings Grampa to a plane hidden in the jungle which he turned into a secret nightclub, where such nefarious types as drug lords and the founder of Ticketmaster are enjoying their exiles. Seeing how much fun life is there Grampa decides he wants to stay in Cuba. The Simpsons family tries to talk him out it. As they all board the plane it turns out that Isabella is a C.I.A. agent who tries to search for and arrest American refugees and transport them back to the U.S. Thus, Grampa and the family are brought back home but Grampa does retain some better feelings when he's back in the U.S.
Tony Sokol of Den of Geek gave a positive review of the episode, giving it a 4/5, adding, "'Havana Wild Weekend' is a fun episode in what is shaping up to be a far better than average season. The jokes come fast, there are a few great setups and the locations are great. The Simpsons have visited almost-countless countries in their time.. There, as here, well, not here but in Cuba, the Simpsons fall in love with the locations and are far more respectful than they have been in the past." Dennis Perkins of The A.V. Club gave the episode a C+ stating, "in the long and storied history of Simpsons travelogues, 'Havana Wild Weekend' is as sure to be forgotten as is poor old Abe." "Havana Wild Weekend" scored a 3.1 rating and was watched by 7.13 million people, making it Fox's highest rated show of the night.
