Main photo: Vanessa Dudley celebrating her 25th Rolex Sydney Hobart at the 2023 Prizegiving Ceremony with her medallion. Photo: CYCA/Ashley Dart

When the modified Joubert 42, Tilting at Windmills, docked in Hobart this afternoon, crew member Vanessa Dudley became just the third woman to achieve the milestone 25 Sydney Hobarts in the Cruising Yacht Club of Australia’s race.

The respected sailor would have got there sooner, but COVID stopped her in 2020 and then a sailing injury weeks before the race ended her chances in 2021.

In 2022, Dudley sailed her 24th on King Billy and was asked to sail on Tilting at Windmills for the 78th running of the race, so was able to put her 25th to bed. And what a way to do it, in one of the toughest races in a long time.

“I never planned to do 25, it just happened that way,” she said after docking in Hobart.

On her 25th, Dudley, known as ‘Duds’ to friends, said from the race course earlier today: “We’re under kite matching racing the blue boat (Ian Johnston’s Zephyr Insurance Masters). They’re only 20 metres away and have been with us since the top of Tassie.

“We got to 40 knots in Bass Strait, but we’re on a very strong boat. It’s really seaworthy and well mannered.

“It’s been memorable, yeah – beating, beating. Every time you turned a corner, it was more beating. I’ve only done one slower race, when we got here on New Year’s Day on All That Jazz,” Dudley said of the 1993 race, one of the worst on record and some claim THE worst on record.

“It’s been bash, bash, bash, but we weren’t alone, we’ve had competition around us all the time,” she said.

Dudley, who is predominantly a helmswoman, did her first Hobart on Bill Gilbert’s brand new Farr 37, Southern Cross, in 1984.

“There’s been so many highlights, but the standout was my first with Bill Gilbert. For getting the opportunity at a time when there weren’t that many women doing the race.

“It was a really rough one, one of the worst races. We suffered damage and had to withdraw, but the crew was so calm and experienced and their attitude was good. So I knew from the start what the race could be like. After that, it comes as a pleasant surprise when it’s nice.”

The 1984 race, again, one of the worst on record.

“Coming second in 2018 was a highlight,” she said of sailing with Stacey Jackson’s all-female crew aboard Wild Oats X. They finished little more than 13 minutes in arrears of Alive (winner that year and again this year). Both boats were Reichel/Pugh 66s and the two engaged in an epic race-long fight.

“Four years with Bill Wild on Wedgetail was fantastic. Sailing with Syd (Fischer) for the first time on his TP52 Ragamuffin in 2011 and coming third overall – and then sailing on his 100 footer for the next four races were all special.

“I never imagined I’d get to sail on boats like that,” the Sydney sailor said.

“All the owners that make it possible for us to race, all the sailors I’ve sailed with and the sailing community as a whole make this such a great sport.”

This year, Duds came to the race fresh from placing second overall at the ILCA 6 (ex-Laser Radial) Great Grand Master European Championships in Brittany, France. She led till the last day and finished one point behind the winner and won the Women’s division by a massive 71 points.

Dudley was an adept Moth sailor, the first woman skipper of an 18 foot skiff. Like her good friend Adrienne Cahalan, she remains one of the humblest sailors you could meet.

Di Pearson