In 2024, the Rolex Sydney Hobart Yacht Race (RSHYR) takes on an added layer of excitement as it will serve as a key qualifier for one of the most challenging ocean races in the world – the Melbourne Osaka Cup. The iconic double handed race, launched in 1987, is held every four to five years. Next year is the ninth edition, with an impressive 25 entrants. Many of the competitors will set sail from Sydney Harbour on Boxing Day in the 628 nautical-mile race. Not only are they participating in Australia’s toughest race, they’re racing to secure their ticket for the gruelling 5500 nautical mile journey to Osaka, Japan.
They are required to complete no less than 400 nautical miles with the Melbourne Osaka Cup crew on board no less than six-months before the event. For these competitors, the Sydney Hobart is the stepping stone to the ‘big thing’.
The Osaka Cup is Australia’s longest Category 1 race and is the equivalent of completing eight back-to-back Sydney Hobarts. In the 2018 Melbourne Osaka Cup, Australia’s Rupert Henry and Greg O’Shea not only won but also broke the race record. They completed the race on the JV62 Chinese Whisper in a jaw-dropping 21 days 12 hours 41 minutes and 13 seconds. To put this in perspective, most yachts usually take around 35 days to complete the race.
The staggered race start is in Portsea, Victoria from March 9-30. The slower yachts will depart early, while the faster yachts start later, with the main start on March 16. The competitors will head off into a thrilling journey through diverse and challenging conditions. After navigating Bass Strait and Australia’s east coast, they will sail against the powerful East Australian Current into the steady South Easterly Trade Winds. The challenge deepens through the Solomon Islands and the unpredictable doldrums near the equator. From there, the North-Easterly Trade Winds and equatorial current lead to the final test, battling the Kuroshio (Japan Current) along the Pacific coast of Japan.
The adventure concludes in the port of Osaka on Honshu, Japan’s largest island. Eight yachts in the 2024 Rolex Sydney Hobart will compete in the Osaka Cup. Of these eight, seven will sail double-handed to Hobart. These feature the father and son team of Tristan and Ken Gourlay on Blue Moon, Saskia Groenin’t-Woud and Maud Demazure on Celeste, Grant Chipperfield and Peter Dowdney on Joker X2, Jim Oosterweghel and Ian Goldsworthy on Lord Jiminy, Annette Hesselmans and Sophie Snijders on Fika, Darrell Greig and Kevin Le Poidevin on Roaring Forty and Christopher Canty and Shona Forsyth on Sailor Moon.
The Joker crew
The 2025 Melbourne Osaka Cup has been a goal for Victorian sailors Grant Chipperfield and Peter Dowdney. When the pair raced in the inaugural Double Handed Division in the 2021 Sydney Hobart on the Elliott 1250 Tourer, Joker on Tourer, they used the race as a warmup for the big event. They placed fourth on Double Handed Line Honours that year and placed third in the double handed division of the Ocean Racing Club of Victoria’s (ORCV) 2022 Melbourne to Hobart Ocean Yacht Race, (aka the Westcoaster). They are not short on offshore sailing experience. Dowdney has competed in 17 Sydney Hobarts. A standout was his role as crew on the late Syd Fischer’s line honours winning yacht Ragamuffin for the 1988 edition. Dowdney and Chipperfield have since upgraded to the French built, American designed J133. Keeping on theme, they named it Joker X2.
They wanted a light yacht that could serve them in all conditions, compared to Joker on Tourer which has been compared to a “caravan”. They have faith that the 43-foot, eight tonne yacht will do the trick. All-female crewed competitors Annette Hesselmans and her 26-year-old daughter Sophie Snijders will be on board the blue water cruising yacht – the Najad 1490 Fika. The duo will become the first mother-daughter double handed team to compete in both the Sydney Hobar and Melbourne Osaka Cup. The 2025 race isn’t Hesselmans’ first rodeo. In 2018, Hesselmans and her husband Gerard Snijders placed seventh On Line honours on the Redford 12.2 Red Jacket.
This will be Hesselmans’ second Sydney Hobart. Sailing runs through the veins of Hesselmans and Snijders. Hesselmans runs her Royal Yachting Association certified sailing school on board Fika. Snijders and her partner Slim document their circumnavigation of Australia on board their yacht Nakama. Although this will be Snijders first Sydney Hobart and Melbourne Osaka Cup, double handed sailing is part of her DNA. Snijders has been offshore sailing with her “crazy parents” (said with affection) from the age of one. Her parents sold their home and bought a boat, which they sailed from Port Phillip Bay, Victoria to Lizard Island, Great Barrier Reef. In 2018, the pair delivered Red Jacket home from Osaka, with one other person.
Later that year, along with two other female crew, Hesselmans and Snijders raced Red Jacket in the Four + Autohelm division of the ORCV Westcoaster. This will be the Hesselmans and Snijders longest race together. It is all about having the “right mindset” as they take on the physical and mental challenges of racing for over a month. They will work on a three-hours-on, three-hours-off watch system.
“Most of the time you are very much the sole sailor,” Hesselmans said. “You do get pretty tired and as the race progresses it’s harder and harder to wake each other up. It’s almost like a hook in each other’s toes to try and wake each other up for watches.” Hesselmans described the 2018 race as “life changing” and said looked forward to sharing that experience with her daughter next year. “It’s an incredible race,” Hesselmans said. “It’s such an experience and you get into such a beautiful rhythm with your co-skipper.” The Nautor Swan 38 Celeste joins Fika as the second all female crewed yacht competing in both races.
Aboard Celeste is Gladstone-raised Saskia Groen-in’t-Woud and French-woman Maud Demazure. Among many of her sailing escapades, Demazure was watch captain on Wayne Seaward’s Beneteau Oceanis 473 Cyan Moon when it placed first on PHS Overall in the 2022 RSHYR. The two successful sailors, businesswomen and mothers will raise funds for the non-for-profit organisation Jean Hailes in tandem with their Melbourne Osaka Cup campaign. Jean Hailes’ is a “non-for-profit organisation dedicated to improving women’s health across Australia”.
Another offshore challenge for Roaring Forty
Another Melbourne Osaka Cup competitor who could be regarded as an adventurer or absolutely mad is Kevin Le Poidevin. Le Poidevin and Darrel Greig co-skipper the Lutra Boc Open 40 Roaring Forty. Le Poidevin was the only Australian entrant in the Global Solo Challenge (a single-handed, non-stop race around the world) which commenced in Spain in 2023. But he retired in February this year when the timing to pass Cape Horn wasn’t going his way, especially if he wanted to be ready for the 2024 RSHYR come December. Le Poidevin has a deep love for offshore sailing. After the Melbourne Osaka Cup, he plans to circumnavigate Australia in record time.
Alive racing in the 2018 Rolex Sydney Hobart Yacht Race fully-crewed. Alive went on to claim its first Overall victory that year. Photo: ROLEX | Carlo Borlenghi.
Alive swaps fully-crewed for double-handed
Another yacht competing in both the Sydney Hobart and Melbourne Osaka Cup is Phillip Turner’s Reichel Pugh 66 Alive, co-skippered by Duncan Hine and Glenn Miller. Alive will compete in the fully-crewed division for the Sydney Hobart, as the Tasmanian entrant looks to defend its 2023 win on IRC Overall. It will then be converted into double-handed mode ahead of the Melbourne Osaka Cup. In early November, the duo completed the compulsory qualifying passaged ahead of the Cup. Hine laughed when it was noted that it was “awesome” that he and Miller are racing the 66-foot canting keel yacht in the 5500nm race. “Awesomely dumb, you could say that,” Hine said.
“It’s always great to do these things on fast boats, otherwise it would be a long trip, wouldn’t it?” Hine is wary but also excited to take on this mammoth task of the Melbourne Osaka Cup. “It’s one of those bucket list races,” Hine said. “It’s not very often your childhood dreams can unfold.”
