According to the Royal Western Yacht Club of England, it all started in 1956 with a man named Herbert “Blondie” Hasler. Hasler dreamed up the idea of a single-handed transatlantic race that started in southern England and ended in New York. He issued a press release, and 100 yachtsmen expressed interest in participating, but only eight officially entered the race. And when it was time to set sail in 1960, only five cast off their lines—with nothing but handheld sextants and compasses to guide their way.

One of those five was Sir Francis Chichester, who had served as an air-navigation expert during World War II, and who had taken up ocean sailing in 1953. Chichester’s steed was the Gipsy Moth III, by far the longest boat in the race at a length overall of 40 feet. Hasler competed in his 25-foot modified Nordic folkboat Jester. One particularly intrepid soul set course aboard a 21-footer.

There were no satellite phones at the time, so nobody really knew how things were going out on the Atlantic. As the days ticked on past one month, concerns grew on both continents about the competitors’ well-being. And then—after 40 days, 12 hours and 30 minutes—Chichester sailed Gipsy Moth III into view, winning the race.

According to the yacht club, Chichester remarked, “Every time I tried to point Gipsy Moth at New York, the wind blew dead on the nose. It was like trying to reach a doorway with a man in it, aiming a hose at you. It was much tougher than I thought.”

Hasler arrived eight days later, and all the rest of the boats followed, with the 21-footer arriving last, after 74 long days. The race became known as the OSTAR, which stands for Observer Single-handed Transatlantic Race, thanks to sponsorship by The Observer newspaper. The race continues to be held today, with the Royal Western Yacht Club of England still organizing it. This year’s start date is May 15. 

This article was originally published in the May 2022 issue.