Round the Island Race was established by the Island Sailing Club in 1931. The original idea came from Club member Major Cyril Windeler who envisioned a race around the Isle of Wight that catered for smaller boats, thus championing ‘The Friendly Club’s’ values of inclusive sailing.
Major Windeler commissioned a trophy from Bruce Benzie, the Cowes jewellers, after seeing one he liked in a goldsmith near a Roman wharf in London. The Gold Roman Bowl has been the main event trophy ever since time. The first race attracted 25 entries and was won by skipper Peter Brett, who competed in the 22-foot Cornish fishing boat ‘Merry Conceit’. Major Windeler commissioned a second trophy, the Silver Roman Bowl, after skipper Chris Ratsey was accused of breaking the rules and declined the winner’s trophy. The Silver Roman Bowl has been awarded for the second yacht overall ever since. Ratsey was the undisputed winner of the Gold Roman Bowl in 1938. Major Windeler finally won the Gold Roman Bowl in the seven-ton auxiliary cutter ‘Kalliste’ in 1939.
The event, along with all private leisure sailing, was banned for the duration of World War Two and resumed in 1946. Numbers have steadily increased over the years with a fleet of 1813 taking part in the Club’s centenary year in 1989. More than 1200 boats and 8000 competitors took part in the 90th year of the Race in 2021.