One of the first legendary sections of the expedition was the Darién Gap, the roadless region between Colombia and Panama.
Dense rainforest, rivers, mud, wildlife and armed groups make the area exceptionally dangerous. It interrupts the Pan-American Highway and remains one of the most difficult overland passages between South and Central America.
Bushby crossed it during a period of serious armed conflict in Colombia. His military background helped him manage navigation and survival, but it could not eliminate the risks created by terrain and human activity.
After the Darién, he continued through Central America, Mexico and the United States.
The journey depended not only on endurance but also on strangers. People offered water, food, shelter, directions and companionship. Those encounters became one of Bushby’s recurring explanations for why he continued: the world he experienced on foot was often more generous than the frightening world shown in headlines.
The Bering Strait
The Bering Strait was one of the expedition’s defining obstacles.
In 2006, Bushby and French adventurer Dimitri Kieffer crossed from Alaska toward Russia over shifting sea ice, walking when possible and swimming between ice sections when necessary.
The crossing was dangerous in ways that were difficult to predict. Sea ice moved. Open water could appear where solid ground seemed to exist. Temperatures threatened exposure, while navigation and timing were critical.
Reaching Russian territory did not end the difficulty. The two men were detained because they had entered without passing through an official border checkpoint.
The incident introduced a problem that would repeatedly shape the expedition: physical possibility did not guarantee legal permission.
Bushby had found a way across the ice, but international borders are not governed by the logic of an adventure route.
Years of negotiation and visa complications followed.
A journey repeatedly interrupted
The expedition’s timeline can look almost impossible until its pauses are considered.
Bushby did not walk continuously every day for 28 years. Funding shortages stopped him. Visa limits forced him out of countries. International events closed routes. The COVID-19 pandemic created another major delay.
At times, he lived in Mexico while trying to finance or legally unlock the next stage. When permission arrived, he returned to his last coordinate and continued.
Critics might argue that these interruptions undermine the romance of a single continuous walk. Bushby’s standard is more precise: the geographic line of progress must remain unbroken.
He never used a vehicle to skip a difficult section of that line. Administrative travel occurred outside the expedition, and every restart took place where the previous stage had ended.
That method required meticulous record-keeping as well as patience.
The walking was only one part of the challenge. Bushby also had to preserve the possibility of continuing while governments, sponsors and circumstances changed around him.
A world transformed during the walk
When Bushby left Punta Arenas in 1998, Google did not yet exist as a public company. Smartphones, social media and satellite navigation had not become ordinary parts of daily life.
Early in the expedition, he relied on paper maps, film cameras and limited methods of communication.
By the final European stages, people could track his location, watch updates and send messages instantly. A journey that began in the era of postcards arrived in the age of TikTok.
The change altered both logistics and public attention.