Flying Jenny Looks to Maintain a Winning Streak in VX One Caribbean Cup series
Posted in 2025, VX One Caribbean Cup
Photo: Ingrid Abery
Rob Greenhalgh (GBR) has competed in and won both the Volvo Ocean Race and the Extreme Sailing Series; in short he’s no slouch on the racecourse. This week he has his work cut out for him on a much smaller boat than he typically sails, racing the BVI Spring Regatta with Sandy Askew (USA) and Drew Barnes (GBR) on the VX One Flying Jenny. It’s Greenhalgh’s third time doing Spring Regatta, he raced it previously on the Cape 31 Flying Jenny.
Greenhalgh currently lives in Sydney, Australia working for North Sails. He got to know David Askew sailing with him on the Volvo 70 Wizard, competing in the RORC Transatlantic Race and the Fastnet, as well as other notable international events, and the relationship evolved from there. He brought Barnes into the Flying Jenny programme several years ago.

“I’ve been sailing with Sandy now for two years, mainly because of Rob and it’s been going really well,” Barnes said. “We’ve done the Cape 31 circuit in the UK, some Melges 24 sailing in America, and now we’re doing the VX One for the first time as a team and it’s really good fun.”
At heart Greenhalgh and Barnes are dinghy guys – moth sailors and foiling boats – so they’re enjoying being on the performance-forward VX One, taking first place at the St Thomas regatta last week after just two days training in the boat.
“Obviously as your sailing evolves and progresses it branches out into bigger boats but it’s fun being on the VX One and sailing it for the first time,” Greenhalgh commented. “The wind conditions this year have been pretty fantastic compared to last year, the trades are pumping. Last week, other than one cloud going through which softened the wind, we had twenty+ knots every day. Friday looks full-on for the first day of racing in Spring Regatta, then it looks like beautiful trades for the rest of the event.”
Preserving the smaller boats was key this week so Flying Jenny stayed shoreside on the lay day and focused on fully checking all the systems in anticipation of big breeze this weekend.
“We’ve had a week of sailing the boat in hard conditions so we did a full systems check throughout,” Greenhalgh noted. “We had the rig out the other day having a full check on that and on the lay day we put our race sails on and did a few other last-minute checks like diving the boat and getting it ready for sailing on Friday. Conditions here are wavy so it’s pretty full-on for these boats, and we could take another 10-20 kilos for the breeze, but we are what we are!”
Barnes jumped in, “We’ll just have to hike hard, get our asses over the side! Friday will be a big day,” he laughed.
The “youngster” on the boat, Barnes is enjoying being on a small team and playing on a more skiff-like boat.
“The VX is really good, it feels like root sailing, it feels like you are younger again; it’s a bit like a 49er, very skiff like in that sense,” Barnes commented. “It is quite fun to have a smaller team with the same number of jobs; it adds that extra challenge to the boat. Last week’s regatta was actually pretty tough – we did four races a day which was good fun but we weren’t actually expecting to do that much – it was a lot of hiking! But, it was a really good challenge and added to the competition and toughness of the event.”
The competition in the VX One fleet is tough anywhere, but especially this week with four Olympians and some eight world champions in four boats alone. Looking for another win this week which will award them the first-ever trophy awarded for the two-part VX One Caribbean Cup series, sponsored by Evolution Sails, Greenhalgh voices cautious optimism.
“Wizard with David Askew, Charlie Enright and Patrick Farrell will be good, there are other boats who have upped their game for this weekend, and obviously there are also the regular VX sailors who are really good,” Greenhalgh said. “You can’t really pick it; you just have to go out, do your best and see where the chips land. People can up their game quite easily and hopefully we’re still at the level we were at but things change very quickly. Some teams improve and some can weaken slightly. Fatigue comes into it, different conditions, different sea states, the racecourses may not suit some people. We just have to chip away and work hard.”
Barnes added: “The starts are a lot harder in one design racing – the boats are the same and it is a challenge; these conditions make it more challenging so it’s really epic to have ten boats on the line this week. We’re really looking forward to getting a new top speed – we got 20.6 knots in St Thomas, supposedly someone has hit 24 knots in the VX One before but we think that’s quite fast. But this weekend – tomorrow especially – may be the weekend to try it, we’ll see what happens!”
“It’s a great regatta which is why we keep coming back,” Greenhalgh said. “We’ll be back next year, probably in the VX just for simplicity.”
Editors note:
The VX One fleet is racing in the Virgin Islands in large part due to the hard work of Tim Pitts, fleet organizer. Pitts grew up in St Croix and it’s been a long-time dream of his to bring the VX One fleet to his home waters.
“This is a homecoming for me, I know a lot of the faces on the docks and there is no better sailing in the world,” Pitts commented. “As soon as I saw the VX One twelve years ago which is when I got involved in the fleet, this is where I wanted to sail. It’s been a ton of work pulling this off but I really won when eleven boats hit the water last week in St Thomas, and now this week in the BVI, it just means so much to me.”