Much like the Oxford Cambridge Far Eastern Expedition undertaken five years earlier, the Trans Darien Expedition of 1960 pitted another pair of Land Rovers, this time Series 2, against the dense jungles along the border of Panama and Columbia. The region is called the Darien Gap and is widely considered to be the most impassable stretch of land on the planet. At the time there was no overland route connecting North and South America – all travel had to be accomplished via boat or plane. In 1957 an exploratory committee was assembled to assess the feasibility of constructing a Pan-American Highway that would connect the two continents. To get a better understanding of the terrain the committee commissioned an overland expedition from Panama City to Bogota.
The expedition consisted of two Land Rover Series 2 and a Jeep Willy, and was crewed by Amado Araúz and his wife Reina, Otis Imboden, Richard E. Bevir, Terrence Withfield, Ilse Abashagen and later with José A. Saénz and Bolívar Araúz. The expedition had to hack their way through the thick underbrush, wade through endless miles of mud, winch their way over mountains, and forge through murky rivers of questionable depth. Some days the company could only manage 5 kilometers of forward progress. In the end, it took a total of 134 days to cover just 500 kilometers, although by all accounts they were the most treacherous 500 kilometers ever crossed. The Trans Darien Expedition was a success, which inspired subsequent crossings by other expeditions, however for a myriad of political and environmental reasons construction of the highway never materialized. Still to this day there is no overland route from North America to South America.