In a random twist of events, Palin pops up in the Florida Keys and sees a Hemingway look-alike contest at the local restaurant. He also goes to visit a man who boxed with Hemingway. Going to Uganda, Palin looks at the site where Hemingway's plane crashed and the newspaper headlines declared that the famous author and his wife were dead. This was not the case, as Palin soon flies over to Venice, Italy, to keep following Hemingway's always moving footsteps. In Venice, Palin walks in the midst of an ancient festival that had been gone for 200 years and was revived only in 1975. The people wear masks and cloaks, so as Palin decides to get into the spirit, he dresses up as a Gumby from the Monty Python television series. After this, Palin goes to a dinner before the duck hunt begins, and interviews the Italian people at the meal. Putting on a jacket and gloves, Palin and the Barone, his duck-hunting partner, wait for three and a half hours for a duck to come.

In Chicago, Palin spends a bit of time exploring the city before going to Hemingway's birthplace, Oak Park. After strolling through Hemingway's first home and singing some of his childhood songs , he goes back to Chicago and enters a local shooting range, hoping to be like Hemingway. Mostly, Palin just jumps at the recoil. Hopping up to Michigan, Palin looks at the area where Hemingway first learns to fish, and attempts to catch a few himself. He finds none and ends up hooking the cameraman's ear. Going to the local grocer, Palin asks for things that might have been on Hemingway's grocery list to see if the modern grocer would still carry it. In the process of asking for canned meat, ("We have Spam," the grocer says,) he ends up singing the Spam song from the famous Monty Python aptly named Spam sketch, and then off he goes to Italy. In Italy, Palin goes to the area where Hemingway was wounded and supposedly buried a ten pound note in the ground. After a fruitless search, Palin buries his book in the ground. After attempting to drive an Italian ambulance and become a Red Cross nurse, he ends up travelling into France. Paris, France was "...the city I love most in all the world," according to Hemingway. Now Palin goes through the City of Lights and reenacts perhaps the strangest part of Hemingway's life in 1928- when the writer was reaching for the string for the lavatory, he ended up pulling the skylight string, and the pane of glass crashed on top of his head.

After no luck, Palin hops down to Cuba where he finds many Hemingway leads and visits his home and hotel room. Many failed attempts to interview President Castro are made, and Palin, after waiting a few extra days to have an interview, jets off towards the American West. In the last stretch of Hemingway's life, Palin becomes a temporary cowboy at a dude ranch in Montana and succeeds in roping the camera operator. After rounding a few cows, Palin goes to Ketchum, Idaho to visit Hemingway's grave and professes that "I'm still looking for some sort of approval from him... some sort of nod of acknowledgment from Hemingway." The grave obligingly replies, "Bull-s***."

The programme starts out with Palin reading a novel of Hemingway and then, after being chased by a fake bull, he ends up in Pamplona, Spain. There he watches the famous bull run and then goes to interview a professional bull fighter. Hemingway loved the bull run, and Palin confides that it must be an age thing- he can't stand to watch it. Travelling to Africa where Hemingway did his safaris, Palin goes to a local Masaicircumcision where the teenage boys are dressed up in finery. "Which of you is the most beautiful here?" he asked. "We are all beautiful," replies the boy, "except you!" Afterwards, he catches a view of Mount Kilimanjaro, Africa's highest point.