The skippers competing in the annual Rolex Sydney Hobart Yacht Race dream of winning a top trophy in this challenging offshore race. This year, 10 of them will be women.
While a female-skippered team has not won the Tattersall Cup, which is awarded to the race’s overall winner, more women have been competing in the race as skippers the last few years. It reflects the expanding ranks in sailing of experienced women, the creation of the race’s two-handed class and an uptick in the number of female boat owners.
Women have been participating in the Sydney Hobart race since 1946, with Jane Tate aboard the Active and Dagmar O’Brien on the Connella. The first all-women’s team, skippered by Vicki Willman, raced in 1975 aboard Barbarian, a 38-foot yacht.
This year, 10 women plan to compete as skippers and co-skippers. This follows an upward trend: nine women raced in 2022 as skippers and co-skippers, and seven competed in 2021. In 2019, this number was six, while three competed in the 2017 and 2018 events.
“It is a changed world for the better,” said Adrienne Cahalan, a two-time Tattersall Cup-winning navigator. She plans to start her 31st race — a record for women — as navigator aboard the 66-foot yacht Alive this year.
“Women are accepted as equal players and leaders,” Cahalan said of the race, noting that women are underrepresented in the Sydney Hobart only among the professional and big-boat crews.
The race, which starts on Tuesday, began in 1945 and is a serious affair. Six sailors died and five yachts sank in the 1998 event. Veterans call it one of the world’s greatest, and hardest, offshore races.
The 628-nautical-mile course begins in Sydney Harbor. After exiting protected waters, teams turn south-southwest and race down the New South Wales coastline, before crossing Bass Strait. This shallow-water swath separates Australia from Tasmania and can sometimes create boat-breaking waves.
Then, navigators approach Tasman Island before the boats make the final 40-mile push across Storm Bay and up the River Derwent to Hobart.
For women, a big part of their overall increase as skippers, sailors said, was because of an inclusive and welcoming community that helped create opportunities.
“There’s a women’s sailing network in Sydney where there’s a lot of engagement from females,” said Lt. Tori Costello, who plans to co-skipper the Royal Australian Navy’s 40-foot Navy One this year. “There’s been so many more females just being involved, being given opportunities to get out there and race.”
Sailors said this change was helped by the creation of women’s sailing events, including the Australian Women’s Keelboat Regatta and the Sydney Harbour Women’s Keelboat Series. They also cite SheSails, an Australian organization that encourages female participation in sailing, and several active women’s-sailing Facebook groups and clubs, as contributing factors.
Internationally, they point to the Magenta Project, which works to create better equity and inclusion within sailing, as another important element.
“Just about every sailing club I know of has a women’s group actively educating and providing opportunities for women” said Kathy Veel, the owner and a skipper of the 30-foot Currawong and a three-time race veteran. “There are now many very skilled, experienced yachtswomen who seek the challenge of being in charge.”
Another catalyst, sailors say, was the creation of the race’s two-handed class, which debuted in 2021. While most boats racing to Hobart have a full crew, two-handed teams race with just two people.
“Even if you don’t own the boat, the second person in most cases is a co-skipper,” said Wendy Tuck, the first woman to win an around-the-world race as skipper and a two-time two-handed class veteran. “It is a great opportunity.”
While two-handed sailing doubles the number of skipper roles, it requires, and breeds, a high level of competency and trust.
“Two-handed racing is a great format for fast-tracking skills in all aspects of sailing and seamanship,” Veel said.
After all, one skipper often sleeps while the other stands watch.
Many yachts that compete in the two-handed class are about 30 to 40 feet long. This matters, as their smaller sails generate less load than the bigger yachts.
“The smaller size of most two-handed boats makes them very manageable for female sailors,” Bridget Canham said. In 2022, she and Veel became the first all-women’s two-handed team to complete the race; they plan to compete together again this year.
Annika Thomson, skipper and an owner of the 52-foot Ocean Crusaders J-Bird, said that it was not as daunting to race two-handed aboard the smaller boats. She would know: In 2022, Thomson and her husband, Ian, raced their 52-footer two-handed to Hobart.
She was skipper.
“It’s not recommended,” she said as a joke, of racing a big, powerful boat double-handed to Hobart. “We did it, now we forgot all about it.”
This year, Thomson plans to skipper her boat with a crew of 11, including her husband, who will navigate.
While professionally-run yachts often hire professional skippers, many amateur teams are led by owner-skippers.
“Sometimes to take on a leadership role a person needs to create their own opportunities,” Cahalan said. “For example, by buying or chartering your own boat and putting your own team together.”
She isn’t alone in this thinking: Seven of the nine female-led boats are racing with full crews.
“My thought is always, and always has been, if I want to skipper a yacht, I probably need to own it,” Thomson said. “The more women that own yachts, the more women who are encouraged to buy their own yachts.”
Case in point: Of the nine female-led yachts, seven are owned or co-owned by women. These include Thomson’s 52-footer, Hilary Arthure’s 35-foot Wyuna, and Jiang Lin’s 34-foot Min River.
There’s more than pride in vessel ownership at stake. The Sydney Hobart race can award dozens of trophies. Of these, three are specifically reserved for women
For some skippers, these aren’t enough.
“While these trophies are great in that they acknowledge the women who were pioneers and role models in the sport, the prize women really want to win now is the Tattersall Cup,” Veel said.
“I think it’s much more likely a female two-handed boat could win a division,” she said, pointing to the costs and complexities of campaigning a competitive yacht. “But I don’t want to rule anything out.”
Thomson was more optimistic. “It would be really cool if someone took it up this year,” she said, referring to the Tattersall Cup.
Still, she was realistic.
“How long is a piece of string?” she asked, using an Australian phrase meaning that something is only finished when it’s finished.
Trophies aside, sailors said the real rewards of skippering a yacht in this race were camaraderie, teamwork and the chance to lead a team through a demanding test.
Half of the race is “not the best times, and you’re questioning why you’re doing it,” said Costello of the often-rough conditions. “It comes back down to those moments where you’re wide-eyed and it’s a bit crazy out there, and everyone has that knowing look like, ‘OK, we’re going to get through this.’”
And, with more women taking on this leadership challenge, sailors said the race’s future had never looked more inclusive.
“Women are a big part of the population, so we aren’t going anywhere,” said Tuck, who plans to start her 16th race this year as a watch captain aboard Disko Trooper, a 32-footer. “Well, yes,” she corrected, “we are going to Hobart.”
