Pioneered in the Netherlands in the 17th century, competitive yachting (from the Dutch jacht—short for hunting ship) took a turn for the audacious in the 19th century, when sailors began racing from continent to continent in earnest. Since then the sport has charted a course to perhaps the ultimate ocean challenge: the round-the-world race.

The Great Ocean Race, as the newspapers call it, begins off New Jersey’s Sandy Hook point in New York Harbor. James Gordon Bennett, publisher of the New York Herald, helms Henrietta to victory as she reaches Lizard Point, England, in 13 days, 21 hours, and 55 minutes.

After witnessing a 1924 Rhode Island-to-Bermuda race, a young Englishman, Weston Martyr, was so impressed with the concept of long-distance racing that he wrote a letter to an English yachting magazine. “It is,” he wrote, “without question, the very finest sport a man can possibly engage in, for to play this game at all it is necessary to possess, in the very highest degree, those hallmarks of a true sportsman: skill, courage, and endurance.”

The following year, the first Fastnet Challenge Cup, spearheaded by Martyr, is held. The 615-mile (990-kilometer) course starts at the Isle of Wight, sails around Fastnet Rock, and on to Plymouth, England. Seven boats compete, only four finish.

In Gypsy Moth III, a 39-foot (12-meter) sloop, Briton Francis Chichester sets out from Plymouth, England, for the first Observer Single-handed Trans-Atlantic Race (OSTAR). He completes the passage in 40 days.

Francis Chichester begins his single-handed circumnavigation in Gipsy Moth IV, a 53-foot (16-meter) ketch, leaving from Plymouth, England. Nine months later he returns, becoming the first person to sail solo around the world with just one stop (in Sydney, Australia).

Chichester’s feat later becomes the inspiration for such races as the Golden Globe, the Whitbread Round the World Race (later renamed the Volvo Ocean Race), and the Vendée Globe.

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