Britannia, built for King Edward VII when Prince of Wales in 1893, was undoubtedly the most famous racing cutter of them all. Hugely successful during her long life, she won 33 firsts out of 39 starts in her maiden season and competed against all the fastest yachts of the day. Sold in 1897 - although bought back for cruising in 1901 by which time the Prince of Wales had succeeded to the throne - her second racing career really came into its own when King George V had her refitted for big class competitions in 1921. Under the King's enthusiastic ownership, Britannia went from success to success. Despite being re-rigged seven times in all, her hull shape was so efficient that she remained competitive almost to the end and was only finally outclassed by the big J-class boats introduced in the mid-1930's. King George V died in 1936 and under the terms of his will, Britannia was stripped of her salvageable gear and scuttled off the southern tip of the Isle of Wight.
Westward was a large racing schooner built by Nat Herreshoff in 1910. Bought soon afterwards by a syndicate of German businessmen who renamed her Hamburg, she was sold back into American ownership after the Great War and resumed her original name.
In 1924 she was bought by T.B.F. Davis and thereafter became Britannia's regular challenger at Cowes. Over the years Davis and King George V developed a fierce though friendly rivalry and Westward became so beloved by her owner that he, like the King, stipulated that his boat was to be sunk after his death.