They survived detention in Ethiopia, an emergency landing in Kenya and two searches for a British retiree who flew off radar in remote locations.
On Friday, however, the 8,000-mile (12,800-kilometer) adventure came to an end as nearly a dozen biplanes, many of them built in the 1920s, flew the final leg of the Vintage Air Rally along the South African coast and landed in the vineyard town of Stellenbosch.
The event, which rumbled to a start in Crete on Nov. 12 with pilots from South Africa, Botswana and elsewhere, raised money for wildlife and other charity projects with the aim of following in the footsteps of pioneering flights in the 1920s.
The route took the pilots along some of the most evocative points in Africa, including a low flight along the Nile from Cairo to Khartoum in Sudan, past the continent's highest mountain, Kilimanjaro, and over the Serengeti game reserve and Victoria Falls.
The organizers, Belgian flight safari company Prepare2go, said the only obligatory equipment for the journey was a sleeping bag, full black tie dress for meeting dignitaries along the way and a beginners' guide to Swahili.
The planes, which were supported by more modern planes and helicopters, did not always have a smooth flight.
On Nov. 25, pilots were detained in Ethiopia for entering the east African country's airspace illegally because of a breakdown in communications, with authorities not informed in time of their arrival. The pilots were held in the town of Gambella, where there is a high military presence due to tensions with neighboring South Sudan.
The rally was suspended while diplomats scrambled to secure the release of the pilots and crew. Several days later, organizers said the pilots got the all-clear to continue their journey.
The planes, one of was flown by the actor Robert Redford's character in the movie "Out of Africa," were cheered by spectators as they flew low over a national park in Kenya's capital, Nairobi.
One plane was not as lucky. Irishman John Ordway and his daughter Isabella escaped uninjured after their 1930s Boeing Stearman made a forced landing on the way to Nairobi after engine failure. Organizers said the crew was not injured, "although the aircraft was irreparably damaged."
Another pilot, 72-year-old Maurice Kirk from Britain, had no satellite tracking or working compass in his 1943 Piper Cub and went missing for two days between Sudan and Ethiopia. He was later found to be among the pilots detained in Ethiopia.
It was the second time during the rally he had gone missing, prompting organizers to ask him to withdraw due to a "mismatch in expectations."