Round the Island Race passes Hurst Castle 2024 © Thomas Wilson

Round the Island Race approaching Needles lighthouse © Paul Wyeth

Passing the Needles in the Round the Island Race © Paul Wyeth

Big boats, small boats, state-of-the-art boats and boats that have seen better days: all take part in this annual handicap event.

Inaugurated in 1931, the race was dreamed up by Major Cyril Windeler, who went on to win it himself in 1939.  From the start it has been organised by the Island Sailing Club, and – except during World War II and the 2020 Covid lockdown – it has gone ahead every year since.

That first race, in 1931, attracted just 25 entries competing for the coveted Gold Roman Bowl; today some 10,000 sailors take part in around 1,200 boats, making it one of the largest mass-participation events in the UK.

From the start point off Cowes, the 50.1 nautical-mile course runs anti-clockwise around the Isle of Wight. Nowadays competitors set off in groups, depending on tides so be prepared for an early start if you want to catch the action from Hurst Castle one of the best vantage points.

Such is the appeal of the race that participants range from local sailors to top politicians and Olympic medallists. In 2013, Sir Ben Ainslie in his AC45 catamaran finished in less than three hours, breaking the course record, while during the 1970s serving prime minister Sir Edward Heath lifted the trophy three times in a series of yachts named Morning Cloud, adding a fourth victory a few years later.

More locally, success came for Keyhaven sailors Richard and Harvey Bagnall in 1977, the Queen’s Silver Jubilee year, when they took the trophy in their 30ft boat – aptly named Silver Jubilee.

Richard Bagnall receives the Gold Roman Bowl, 1977 © Joy Warren

Courtesy of the British weather, there’s nothing predictable about the race.  In 2024,  with 3–4m waves and winds gusting up to 45mph, some classes were cancelled entirely. Of the rest, many retired before reaching the Needles, and only 154 completed the course.

Conversely, lack of wind creates its own challenges. In 1933 two boats took more than 24 hours to return to Cowes in 1933, though nowadays there’s a cut-off time.

Whatever the weather, it’s a thrilling spectacle – so make sure to take your place at Hurst Castle for the next Round the Island Race.