The programme starts out with Palin sitting on a beach reading a novel of Hemingway. 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 matador. Hemingway loved the bull run, and Palin confides that it must be an age thing - he can't stand watching it. Travelling to Africa where Hemingway went on many safaris, Palin goes to a local Maasai circumcision 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.

In a random twist of events, Palin pops up in the Florida Keys and sees a Hemingway look-alike contest at the local restaurant in Key West. He also goes to visit a man who had boxed with Hemingway. Going to Uganda, Palin looks at the site where Hemingway's plane crashed, after which the newspaper headlines incorrectly declared that the famous author and his wife were dead. Palin soon flies on 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 forgotten for 200 years and was revived only in 1975. The people wear masks and cloaks, so Palin decides to get into the spirit and dresses up as a Gumby from the Monty Python television series. After this, Palin goes to a dinner before participating in a duck hunt, and interviews the Italian people at the meal. Putting on a warm jacket and gloves, Palin and the Barone, his duck-hunting partner, wait in vain for three and a half hours for a duck to come.

Palin flies to Cuba where he finds many Hemingway leads and visits his former home and a hotel room he often stayed in. 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. Following the last stretch of Hemingway's life, Palin becomes a cowboy at a dude ranch in Montana and succeeds in roping the camera operator. After rounding up a few cows, Palin goes to Ketchum, Idaho to visit Hemingway's grave. He 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***.