The first record of Uffa racing in Cowes Week is in 1925. He had designed and built a National Fourteen for himself called Ariel, and she was placed first on the Friday of Cowes Week in the Cowes Royal Town Regatta. Two years later the inaugural Prince of Wales Cup race for Fourteen Footers was held on the Monday of Cowes Week from the Royal Yacht Squadron line, where Uffa's experimental Fourteen Radiant was placed second.

From the early 1950s Uffa became a major attraction in Cowes Week, largely due to his friendship with Prince Philip, Duke of Edinburgh. He was often seen aboard Bluebottle, the Dragon given to Princess Elizabeth and the Duke of Edinburgh by the Island Sailing Club, and Coweslip, the Flying Fifteen gifted to Prince Philip by the town of Cowes.

Prince Philip normally raced at least one day in both the Dragon and Flying Fifteen classes during Cowes Week, with Uffa often as crew. On one occasion Bluebottle broke a stay early in the Dragon race and retired; Prince Philip and Uffa jumped aboard Coweslip and went on to race in the Flying Fifteen class.

Uffa's last home, the Commodore's House overlooking the Cowes waterfront, was a fine venue for royal visits: restricted access from the road, good access by sea, and social occasions planned around the tides so the royal barge could deliver and collect his guests.

To mark the bicentenary of Cowes Week in 2026, the Commodore's House will host an exhibition, Sailing Through Royal History, presented by The Royal Yacht Britannia Trust, with part of it dedicated to Uffa. It runs from 31 July to 29 August 2026, and Coweslip will be exhibited on the quay for most of August.