When Todd McGregor signed up for Emirates Airline’s frequent flyer programme, Skywards, he was more concerned with getting an upgrade; sailing off Dubai with some of the world’s best yachtsmen was not in the fine print.

This week McGregor, as well as 30 other guests and media, earned the bonus of match-racing around the harbour off Dubai International Marine Club with members of Emirates Team New Zealand, the No.1 challenger for the most prestigious prize in sailing – the America’s Cup.

“Admittedly, I haven’t done much sailing so I didn’t really know what to expect but it was great fun and I got a lot of it,” said McGregor, who is the Managing Director of a Dubai-based research and consulting firm.

McGregor sailed in a five-man crew with Emirates Team New Zealand trimmer Grant Loretz and bowman Andrew McLean in charge. Top jockeys Frankie Detorri and Ted Durcan were also among the Emirates Airline guests this week.

Loretz skippered the yacht during the Pro Am match-race while McLean called the tactics and made sure the yacht was sailing fast against some stiff competition from three other crews, one of which included Grant Dalton, the General Manager of Emirates Team New Zealand.

McGregor worked under Loretz’s nose during the match races trimming the mainsail, while the rest of the crew kept the front of the boat trimmed. McGregor said hearing the sailing jargon was another highlight. “It’s easy to think the lingo is too confusing until you hear it in action with professionals using it,” he said.

In the first match race of the day McGregor’s boat was just beaten, but Loretz and McLean came back to win the second and third races convincingly. While the racing was clearly something different, McGregor said it was “just fantastic to be out on the water.”