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- In 1959, a young journalist ventures to Havana, Cuba to meet his idol, the legendary Ernest Hemingway who helped him find his literary voice, while the Cuban Revolution comes to a boil around them.
- The seven teams continue the leg in Cuba as they travel from Havana to Guamá. The team who stole a taxi from another team in the previous leg find the consequences to be far-reaching. A Detour involving two Cuban icons ends with shattering results for one team. The teams receive a surprise when they learn that they must drive to Australia.