Second Wave of Melbourne Osaka Cup Sets Sail

The second start of the 2025 Melbourne Osaka Cup is away, with Japanese entrant Zero leading a fleet of seasoned sailors through Port Phillip Heads. Skipper Katsuhiro Yamada and co-skipper Masayuki Kobayashi onboard Zero are finally racing, setting course for home—5,500 nautical miles away in Japan. 

This double-handed, non-stop, unassisted endurance race, that compares to racing nine Sydney to Hobart races or completing two Atlantic crossings back-to-back. 

Lining up alongside Zero was Jon Sayer, highly regarded as the “king” of the race, competing for the fifth time. In this race, Sayer is sailing aboard Alan Paris’ J99 Learning to Fly from New Zealand. Also on the starting line were local skippers Robert and Michael Bradley, returning with Escapade.

Despite the high-level competition, Yamada remains focused. “We don’t see any boat as a key rival,” he said. “We’ll simply do our best. My dream is for Japanese boats to take 1st, 2nd, and 3rd.” 

Arriving in Australia in mid-January, Zero enters the race well-rested. Kobayashi reflected on their journey, saying, “We weren’t that close before, but after preparing the boat since June, sailing 35 days to Australia, and working through final preparations, we’ve become more like a family.  

“On the boat, you depend on each other, and that trust helps you sleep better off watch.” 

With Australian gifts exchanged and heartfelt farewells shared, skippers Yamada and Kobayashi received a warm send-off from a strong Japanese contingent gathered along the pier. 

With a steady easterly breeze of 5–10 knots, crews hoisted their asymmetrical or downwind sails and powered across the start line. 

For Sayer, strategy, endurance, and pacing are key to success. “It’s a choice—do you want to win the race or enjoy the sunsets?” he explained. “You have to push hard, but not too hard—you need to finish.” 

He believes whoever gets the best start and reaches Brisbane first (based on time) will have a strong advantage. “Once you get north of Brisbane, you enter a trade wind pattern—typically a southeasterly—where the course shifts from reaching to running. That’s the fastest part of the leg up to New Guinea.” 

Reflecting on a previous race aboard Sayonara, where his team took line honours, Sayer recalled the challenge of a fast, rough downwind leg, with a developing low-pressure system making conditions intense. 

The first two to three days will test sailors with shifting winds and strong eastern currents, as a low-pressure system sits between two highs just north of Victoria. Picking the right course will be critical for maintaining speed and positioning in the fleet. 

The chase will continue with the main start coming up on Sunday March 16th at 5 pm off Portsea Pier with a further thirteen yachts stepping up to race.

Follow the fleet as they race towards Osaka via the race tracker https://race.bluewatertracks.com/2025-melbourne-osaka-cup-double-handed-race 

Learn more about the race and competitors via the Melbourne Osaka Cup website https://melbourneosakacup.com/en/home/ 

Find us on Facebook:  https://www.facebook.com/Osakacup2018/ 

Video from the start https://youtu.be/W_ieQo7svAM

M2O Media 

About the Melbourne Osaka Cup: 

Melbourne Osaka Double-Handed Yacht Race: The World’s Longest South-to-North Sailing Event, is about to kick off, attracting both international and local sailing talent. 

Competitors sail non-stop and unassisted on their own boats with just two people onboard, navigating four weather systems over 32 to 35 days. 

This event provides a unique opportunity for sailors, many of whom are Corinthian (non-professional and self-funded), to embark on the challenge of a lifetime. While major shorthanded races like the Vendée Globe and Transat Jacques Vabre feature professional teams, large shore crews, and significant budgets, the Melbourne Osaka Race stands apart by offering accessibility to sailors who do not rely on extensive support teams. 

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