Six mates, a supplied skipper and a good cause. Wednesday’s Upside Cup welcomes sailors and complete beginners alike.
The Upside Cup returns to the Waitematā Harbour on Wednesday 4 November, raising money for Auckland charity Upside Youth Mentoring. Teams of six will head out from the Royal New Zealand Yacht Squadron at Westhaven. Knowing your way around a yacht is optional.
Each crew gets a skipper, which takes care of the experience question. How seriously everyone takes the racing might be another matter. In a previous year’s preview, Upside described the event as “more about helping kids than winning”. It also warned that the volunteer skippers would still do their best to get their crews across the line first. Anyone who has entered a charity regatta will probably recognise the sentiment. Friendly competition can become quite competitive once another boat gets ahead.
Teams enter for $3,500, according to Upside that funds a full year of mentoring for one young person. The charity works with children aged nine to 13, referred through their schools. Volunteer mentors commit to spending time with them each week for a year. Founded in 2006, Upside says it has supported more than 1,000 young people. It reports that 93 per cent of its mentoring matches in 2025 lasted at least 12 months. Its work reaches across Tāmaki Makaurau, with partner organisations delivering the programme elsewhere, including Rodney and Tauranga.
Jesse Tuke is this year’s MC. Viewers of TVNZ’s 2021 America’s Cup coverage will remember him reporting from the water. His sailing work also includes the 2024 America’s Cup in Barcelona and SailGP commentary from its first season. He has had some practice handling sailors with something to say. During the Volvo Ocean Race’s 2018 Auckland stopover, Jesse hosted a public question session with his older brother, Blair. The Olympic champion faced his younger brother on the main stage in the Viaduct, with their mother watching from the audience.
A trophy worth chasing
The 2024 edition drew 11 teams. Light conditions kept the racing more relaxed than some previous finishes. That year the Brotherhood MERX collected the trophy, followed by Broad Reach. A team entered by sponsor Tax Management New Zealand finished third. Upside reported more than $40,000 raised through entry fees and business donations, enough to support 12 mentoring matches for a year. “Every team still brought their all, with fantastic energy, sportsmanship, and dedication to supporting Upside’s mahi,” the charity wrote afterwards. That gives this year’s crews something to aim for, whichever end of the fleet they find themselves in.
