Michael Palin moves from the busy streets of Chicago to a suburb of Oak Park, Illinois. Here, in a town that Hemingway apparently called a place of 'wide lawns and narrow minds', his ambitious and creative mother dressed him as a girl and wrote some melancholy music.

Later, in Michigan, Michael visits the family summer cottage. He tries fishing and shooting, which according to Hemingway's young diaries were his favourite sports. Michael then travels to Europe and arrives at Milan station. After a quick course in first aid, he finds himself behind the wheel of an ambulance. He goes to the Italian front where Hemingway was shot and wounded and ends up at Italy's largest war memorial in Redipuglia.

Michael drives a tank in Paris and visits Hemingway's shoe-box apartment. He ends up in American hospital in Neuilly, after an encounter with a broken lavatory chain and a skylight.

Michael Palin stays in Ernest Hemingway's favourite Cuban hotel and samples a few of his favourite hangouts including Bodeguita del Medio and the Floridita in old Havana. He meets 101-year-old Gregorio Fuentes, considered an Old Man of the Sea, and who sits in the sun, smoking cigars.

He peers into Hemingway's Havana house that has now become a shrine where visitors aren't allowed to tread.

Back in West America, Michael attempts to be a cowboy and partakes in some male bonding while visiting Yellowstone Park. He also visits the house in Ketchum, Idaho where Hemingway died in 1961 and where he was laid to rest.