In 1993, Whitworth and his partner Hilary Yerbury purchased Berrimilla, a Brolga 33 designed by Australian Peter Joubert. Since the purchase, Whitworth has circumnavigated the world twice aboard Berrimilla. The first time began in 2004 when Whitworth sailed to the U.K. via Cape Horn. On the way, Berrimilla was in frequent contact with Astronaut Leroy Chiao, Commander of the International Space Station (ISS) and for much of the time, Chiao was Whitworth's nearest neighbor when the ISS orbit crossed her track. When Whitworth arrived in the U.K., Berrimilla competed in the 2005 Rolex Fastnet Race, finishing 11th overall and second in the double-handed division. After the Fastnet, Whitworth completed the circumnavigation aboard Berrimilla by returning to Sydney, Australia, via the Cape of Good Hope, arriving just in time to sail in the 2005 Rolex Sydney-Hobart race.