For 226 days within 1966 to 1967, Sir Francis Chichester embarked on an unprecedented adventure aboard his trusty 55-foot sailing yacht, the Gipsy Moth IV. The former miner, salesman, land agent, and aviator single-handedly sailed the same path as the 19th century trading ships manned by 20-strong crews that travelled between Europe and the Far East. This endeavour cemented his reputation as the first person to sail around the world alone from west to east.

Photo: courtesy of Chichester Archive/PP

On August 27, 1966, Chichester started off from Plymouth, England aboard the Gipsy Moth IV and sailed the length of the Atlantic Ocean south across the equator for 21 days before arriving at the Cape of Good Hope. Within this time, he quietly celebrated birthday with a champagne cocktail. Then, Chichester made his way to Cape Leauwin and eventually Sydney by day 80. On his way back to Plymouth, he circumnavigated much of the Southern Ocean past Cape Horn on the 157th day, as this was the most direct way to cross Asia-Pacific to South America before the time of the Suez and Panama Canals.

Thousands of people lining the shores of Plymouth cheered as he made his way home after a 47,600-kilometre journey. Not long after, he was knighted by Queen Elizabeth II for his astounding achievement.

Photo: courtesy of Keystone-France/Gamma-Keystone via Getty Images

Throughout his odyssey, he was accompanied by a hardy navigational companion in the form of a Rolex Oyster Perpetual, which took the brunt of harsh sea living like a champ. “During my voyage around the world in Gipsy Moth IV, my Rolex Watch was knocked off my wrist several times without being damaged,” he wrote in a letter in 1968. “I cannot imagine a hardier timepiece. When using [it] for sextant work and working the foredeck, it was frequently banged, also doused by waves coming aboard; but it never seemed to mind all this.”

Photo: courtesy of Sunday Times/Chichester Archive/PPL

To this day, the clipper route remains the most adventurous course on the open sea—being exposed to the fiercest elements and far from land and rescue. Despite this, it was no match for Chichester’s unquenchable thirst for adventure, which then spawned a widespread interest in sailing. Chichester’s solo exploit aboard his mahogany-hulled yacht led to numerous round-the-world races favouring this most testing route.