Sailing legend Penny Whiting's end of an era

Our sailing legend is ready for life on dry land.

By Julie Jacobson
Penny Whiting has just finished cleaning the windows of her Auckland home. She clambers down from the stool, brandishing a squeegee and admires her handiwork.
“Look at them, they’re beautiful,” she laughs, her trademark cackle ringing across the cavernous room that looks out to Cox’s Bay and beyond to Auckland’s Waitemata Harbour.
She has been meaning to clean the windows for yonks, she says, but has never had the time. Until now, that is. The legendary athlete, whose name is synonymous with yachting, is hanging up her sailing shoes.
Retiring. The word doesn’t sit easy with Penny. She’s not had a day off in the 50-plus years she has been running her Penny Whiting Sailing School.
Now 68, she hoped to keep going until she was 70, and as recently as October was toasting the school’s ongoing success at a celebration to mark its half century.
But deep down Penny knew something had to give. A lifetime of hard, physical work combined with a family history of arthritis has taken its toll, and come November when the school should be reopening for summer classes Penny won’t be on board.
She is quick to stress she is not giving up sailing completely but the intensity of teaching, day-in, day-out.
“It feels 100 per cent horrible,” she says, when asked how it feels to let go of what has essentially been her life since 1966.
“I’m not excited about stopping sailing school at all, but I’ve got too much arthritis in my ankles and knees. It’s just physically too tough.”
The venture began as the “ladies only” Lady Penelope Sailing School but she has gone on to teach some 33,000 would-be yachties from New Zealand and overseas. Some of her star students went on to compete in the Whitbread and Volvo Round the World races and the America’s Cup.
She has hosted A-listers such as Muhammad Ali as well as royalty – Prince Charles and Prince Philip – on her 47-foot, self-built keeler Endless Summer.
“Ali was here for a fight so I said, ‘how about I take you for a sail’? He turned up in a suit! I greeted him by running around the mast saying, ‘float like a butterfly, sting like a bee’ and put my dukes up,” Penny hoots.
And then there was investment banker David Richwhite, actor Ian Mune, Jim Delegat (whose yacht Giacomo won last year’s Sydney-Hobart race) and former deputy PM, Sir Don McKinnon.
He was “Always just Don to me”, explains Penny.
“It was only on the fourth lesson that someone sprung him arriving in his ministerial car. He’d whip out of his suit and come running down the dock.”
From a family of sailors, Penny – the oldest of five children – grew up mucking around in boats. She first “raced” as a two-year-old on her father Darcy’s pennant class when he needed a two-person crew. Penny and her teddy bear Teddy Drongo would be roped in as second mate.
“Teddy Drongo – I’ve still got him – would tow behind the boat in his life jacket for the whole race then spend the next week in the hot water upboard until he could go out sailing again on Saturday,” Penny chuckles.
They were the best of times. Penny left school – Mt Roskill Grammar – the day she turned 15. By the time she was 20 she had won a junior title at the legendary Duke Kahanamoku surfing champs in Hawaii, set up the sailing school – running three classes a day, seven days a week from November through to April – and bought her first boat.
“I marched into the BNZ in Devonport with my pigtails and a poodle and told the flummoxed bank manager in a suit and tie that I needed $15,000 to buy a boat. He said they didn’t lend money to people to buy boats, but I walked out with my loan.”
Meanwhile, Penny was also playing Mum to brothers Grant – “who still sends me Mother’s Day cards” – and Paul, after her parents and two younger siblings (Tony and Debbie) set off on a round the world trip.
Tragically Paul, a well-known boat designer and builder in his own right, was lost at sea in 1980.
The Weekly announced the arrival of Penny and Doc’s son Carl in 1981. He has since gone on to be an Olympic and America’s Cup yachtsman.
Penny went on to marry broadcaster David (Doc) Williams – the pair met on the set of Women Superstars, a documentary Doc was producing and Penny was starring in – and have two children; Carl, an Olympic and America’s Cup yachtsman, and Erin, an international show jumper. The pair have now split up.
Penny was a city councillor for a time in the mid-90s (she still chairs the Auckland Zoo Trust) and was awarded an MBE for services to yachting in 1993.
She continued to run the yachting school each summer. She remembers when Carl was little arriving home at 8.30pm to a meal cooked by Doc and a baby son fed, bathed and ready to be put to bed.
“I would come home and wake him up him so I could play with him and feed him. I insisted on breast feeding him for nine months so I got enough contact with him.”
Christmas holidays were spent sailing in the Bay of Islands with the kids. Doc was usually away cricket commentating.
Penny, now a grandmother to four grandsons and a granddaughter, hasn’t seen a New Zealand winter in 18 years, choosing instead to crew for yachts in the Mediterranean, Tahiti, Maine, and Florida. She is steeling herself for the coming months.
“I bought my first coat this week,” she chortles. “I've had sailing jackets but I've never owned a coat. It’s got a hood with a bit of fur fluff around it. Wait until you see me in that!”
And then she looks out towards the harbour through those very clean windows. For the woman who started sailing before there was satellite navigation – she reckons she tried to trick the GPS when she first got it but never could – it hasn’t been an easy decision to bow out.
“I love teaching people to sail. I’m so excited when I see people ‘getting it’. If I was just out there telling jokes and having a drink with them I wouldn’t have been out there for 51 years. I might have lasted five.
“But I’ve been a one-man band forever – the typing, the booking, the fixing the engine, the teaching, the cleaning the boat. I don’t want people to see me hobbling down to the boat. I really do believe I have to retire.”

read more from