Lipton's charitable work was to catapult him into a whole new world. He was, until this time, a man devoted entirely to work. His friendship with the Prince of Wales, soon to be Edward VII, developed rapidly, strengthened by a passion for the shared interest of yacht racing. He was to be as ambitious a sportsman as he was a business man. His very first racing venture was to compete in the world's most famous yacht race: The America's Cup. Between 1899 and 1930 he challenged five times for the Cup, all in yachts named Shamrock, to honour his Irish lineage and friends at the Royal Ulster Yacht Club.
He never managed to "lift that auld mug - surely the most elusive piece of metal in all the world so far as I am concerned". (Lipton, p241) However, thirty years of chasing the America's Cup brought him 'joy... health and splendid friends' and it also kept him "'young, eager, buoyant and hopeful". (Lipton, p242) He also captured the imagination of the American people. He was presented with a solid gold loving cup and a donors' book in which the flamboyant mayor of New York had written "possibly the world's worst yacht builder but absolutely the world's most cheerful loser". (Crampsey, p133)
Even after the transfer of his headquarters to London, Lipton remained a familiar figure in his native Scotland. He was a frequent visitor to Glasgow for business and pleasure. The Erin was frequently seen cruising in the Clyde - especially during Clyde Yacht Week when one of the Shamrocks usually claimed a trophy. Lipton and yacht racing were so popular, that he even makes an appearance in Neil Munro's Para Handy Tales where, much to the relief of MacPhail and the annoyance of the Captain, Shamrock snatches victory from White Heather. In recognition of his popularity and his contribution to yachting on the Clyde, Lipton was presented with the freedom of Rothesay in June 1931.
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