Penny Whiting was born to sail. She arrived in the middle of Auckland's Anniversary Day regatta in 1949, and almost from the beginning her sailing father D'Arcy encouraged her to enjoy the water. She became a swimming champion, then an international competitor in surfing competitions, while also joining in enthusiastically on family sailing expeditions. When she was still in her teens she went into business with her favourite brother Paul, designing and building boats, but this was cruelly ended when Paul was lost at sea in a storm in the Tasman in the late 1970s.
Marriage to sports broadcaster Doc Williams brought two children, Carl and Erin, but Penny continued to sail and teach sailing classes through her famous Penny Whiting school on her boat "Endless Summer". She also found time to coach rugby, writing a sailing book, make a video, speak to business organisations and women's groups, and take charter groups sailing in Fiji and elsewhere. In the 1990s she was elected to the Auckland City Council. In 1999 - 2000 she was an America's Cup commentator for Radio New Zealand. Penny continues her Sailing School every summer. In her spare time she plays tennis and follows the fortunes of her son Carl, who has inherited the family's sailing genes.