Whereas Edward VII, both as King and Prince of Wales, and his son George V remained loyal to their legendary cutter Britannia for forty years, Sir Thomas Lipton did the opposite and spent his long racing career continually upgrading his famous Shamrocks in repeated attempts to win the America's Cup. Lipton, the immensely wealthy tea magnate of Irish parentage, bought his first Shamrock in 1899 and, by the time of his death in 1931, he had owned a succession of six splendid cutters, all but one of which unsuccessfully challenged for the elusive "Auld Mug" as Lipton liked to call the America's Cup. By the time Astra was completed in 1928, Lipton was still racing but using the only one of his Shamrocks which had not been ordered specifically for a Cup Challenge. Designed and built by William Fife at Fairlie in 1908, she was a composite cutter of 175 tons gross (94 net) and was constructed to the International 23-metre class. Measuring 113 feet in length (75½ feet at the waterline) with a 20½ foot beam, she proved a great success and won many prizes for Lipton away from the spotlight of the "Auld Mug's" races off Sandy Hook.
Designed and built by Camper & Nicholsons at Gosport in 1928, Astra was a beautiful Bermudian-rigged composite cutter of 91½ tons gross (83 net) and measured 115 feet in length with a 20 foot beam. Originally built for Sir A. Mortimer Singer, the naturalised British son of the inventor of the sewing machine, she was owned for most of the 1930s by Mr. Hugh Paul who enjoyed much success with her during the so-called 'golden years' before the death of King George V after the 1935 season.