The Island Sailing Club is proud to have organised the globally renowned Round the Island Race for over 90 years.
The annual Round the Island Race, is something of a unique event in the sporting calendar and is the fourth largest mass participation event in the UK (after the London Marathon, Great North and South Runs). It’s rare to find a sporting occasion that encourages enthusiastic amateurs to compete against the elite pros and Olympians of a sport, all on an equal footing and around the same racecourse. This race does just that and celebrates the varied collection of sailors that compete, all of whom love to have a cracking day out on the water.
Few things can compare to the sight of hundreds of boats racing, whether you’re within the fleet yourself or spectating onshore from one of the many excellent vantage points on the stunning Isle of Wight coastline.
Relive moments from Round the Island Race 2024.
The next Round the Island Race takes place on 21 June 2025.
The little sloop Meon Maid II runs down the western Solent under Spinnaker in 1964 (photo: Beken)
A Rich History
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.
Notable Winners
Former Prime Minister, The Rt Honourable Sir Edward Heath KG, MBE, MP won the Race four times during the 1970s and 1980s. Two women have won the Gold Roman Bowl trophy, Mrs H Tobin on ‘Barbar’ in 1954 and Julia Dane on ‘Glass Onion’ in 1982. In the 50th year of the Race in 1986, ‘Paragon’, sailed by Mike Whipp and Olympic medallist Rodney Pattison, flew round the course in three hours 55 minutes and 28 seconds, setting a new course record. In 2006, Jeremy Rogers’ Contessa 26 ‘Rosina of Beaulieu’ became the only boat to win the Gold Roman Bowl for a third time. Sir Ben Ainslie helmed his AC45 catamaran to post the first sub three-hour race in 2013 with a time of two hours 52 minutes and 15 seconds. In 2017, Ned Collier Wakefield finished the race in just two hours 22 minutes and 23 seconds on ‘Concise 10’. Jo Richards has won the Gold Roman Bowl twice; in 2019 and again in 2021, after the 2020 Race was cancelled due to the global coronavirus pandemic.
