The America’s Cup is as tough as it gets. “It’s the highest level of sailing,” says Mr Massimiliano “Max” Sirena. “For sure higher than the Olympic Games.”

Mr Sirena should know. He is about to compete in his seventh America’s Cup, having previously been part of two winning campaigns. The first in 2010 with BMW Oracle Racing, for the US. His second in 2017 with Emirates Team New Zealand. Now he’s back with Italy’s Luna Rossa Challenge as team director and skipper, a role he previously held in 2013.

In January, Mr Sirena will lead his 11-man crew in the Prada Cup in Auckland, a set of match races that will determine which club will meet defenders Emirates New Zealand in the 36th America’s Cup in March. Taking the title from the reigning Kiwis would be particularly sweet: after all, he helped them win it. “I will give a thousand per cent to try to win the Cup for Luna Rossa and for Italy,” he says.

The America’s Cup is a unique challenge. As well as being the oldest trophy in sport, it is also the hardest to win. Since 1851, only four nations have done so (New Zealand, Switzerland, Australia and the US). What sets it apart from every other major sporting event is that the winner (“the defender”) gets to choose the venue for the next edition and in a large part gets to set the rules of engagement. As for the boats, the days of gaff-rigged schooners are long gone. In 2012, the world of top-tier sailing was turned upside down by the introduction of Emirates Team New Zealand’s 72-foot wingsail catamaran, a yacht that skimmed across the Hauraki Gulf on foils – and speeds faster than the wind. Since then, the increases in performance in America’s Cup boats have been greater than at any point in the event’s 170-year history.

“The race used to be way longer, up to two and a half hours,” Mr Sirena says. “Now the race is 25 to 27 minutes, because the boats are foiling. They’re sailing around the same course in four times less.”

The upcoming competition will feature AC75s – 75ft foiling monohull sailboats. Instead of a traditional keel, the leverage to keep them upright is provided by a brand-new concept: hydraulic foil cant arms. As the yacht changes tack, one arm is placed in the water and the other is lifted out – the weight of the airborne arm becomes ballast. This system will help propel the boats across the water at speeds of 50 knots (about 60mph). They can maintain 20 knots even while tacking – turning while sailing upwind – subjecting the crew to serious G-forces as they scurry from side to side in order to steer, an audacious feat of choreography.

“The boat is always on the edge of stability,” Mr Sirena says. “There is a moment when you go from upwind to downwind where the stability is almost zero. It’s up to the crew to keep the equilibrium and go around the markers without actually capsizing.”

Though batteries control the main foils and rudders, everything above the waterline, including every sail control, is powered by the crew – “grinders” using pedestals to generate the critical hydraulic pressure. Throughout the race, their heart rates maintain 180-190 bpm. On-board demands put a premium on power, endurance and mental toughness. “They’re good sailors,” says Mr Sirena. “But they are exceptional athletes.”

Arrangements for this spring’s competition began in September 2017, with Mr Sirena choosing designs for the boat. Much of 2020 was spent training in Cagliari, Sardinia, before the team transferred to Auckland in September. It is not long afterwards when we speak over Zoom and the crew is still in quarantine – a situation they’ve adapted to by having exercise bikes and grinding machines installed in their hotel rooms. “Also, each of us travelled with some gym tools,” Mr Sirena grins, holding up an AquaBell – a portable, water-filled dumbbell. “Because the time we’d lose [quarantining] would be impossible to get back.”

Typically, a day’s training kicks off at 6.45am with a 90-minute workout. The eight grinders will hit their grinding machine – sort of trimmed-down ellipticals rarely found in traditional gyms – doing reps. “You start on level 10 and go up to level 30, on intervals,” says Mr Sirena. “When you arrive at 30 you go back, 28, 27, 26… You do that for an hour.”

Then they’ll get the AC75 on the water and work on strategy for anywhere between five and eight hours. “After that, there is a chance to do another gym session, depending on the fatigue.”

Work stops around 7.30pm, although any downtime after that is at a premium. “I’m struggling to think of a time when someone is still up at nine o’clock,” Mr Sirena says. “You’re normally already in bed because you’re exhausted.”

The crew trains seven days a week. As you’d expect for men who are cardio machines burning between 4,000 and 7,000 calories every day, diet is also important. “You need to eat a lot,” Mr Sirena says. “A big breakfast: eggs, ham, bread. For lunch we have pasta, chicken, rice. A lot of fruit, a lot of vegetables. We avoid sugar as much as possible. But otherwise, a little bit of everything. There’s the opportunity to have a pizza once a week, to go a little bit outside of the rules.” Alcohol: not so much.

“There is time for a beer, or a gin and tonic,” says Mr Sirena, though his expression suggests that time would be better spent doing literally anything else. “But if you don’t respect yourself, you don’t respect the team. There’s always a pay-off.”

The other big factor in training is mental health. The crew spends a good deal of time with sports psychologists, athletes from other sports and Navy Seals. “A lot of exercises to try and keep the pressure under control,” explains Mr Sirena. “We did a lot of training in freediving because the boat could capsize and you could get stuck under the water, so you need to be able to stay calm. People have died in previous campaigns. We need to be prepared.”

To this end, every aspect of their training is recorded. “We’ve got cameras on the yacht, we’ve got microphones everywhere. We are able to record all our communication during the day, so when we are doing a debrief we can flag when someone is yelling too hard, or when there is a problem with communication.”

That’s a lot to be on top of. But like every good leader, Mr Sirena is quick to remind you it’s not about individual glory.

“The whole team is the rock star. It’s not me. It’s not the helmsman. It’s not the boat designer. Everyone is part of the star and we need to make sure everyone is on their 100 per cent. That doesn’t mean there is no conflict within the team. It means we need to be able to talk face-to-face and say, ‘Fuck off to you’, if necessary. As long as, at the end, you achieve your goal.”

Motivation, he says, is not a problem. “The fact that you get a chance to be involved in such an important campaign like this is motivation number one. We are privileged guys doing what we love. I tell the guys there is a train passing in front of you only a few times in your life and you need to be ready to jump on.”

As the three teams – Italy, UK and the US – enter the final stages of training, there is a chance to check out the rival yachts, and their performance, firsthand. It’s a sport in itself. “Each team has its own spy,” Mr Sirena says. “Spying in the America’s Cup is something huge. And historically has been fun as well – there are lots of stories of fights between the spies. So, yeah, we have an eye on the other team and we follow them through our spy. We’ve got video and we get a report every day – we measure the speed of the boat, the way they handle it.

“We have a pretty clear idea of where we are compared to the others. And we think we are not bad at all.” While some parts of the AC75s are stock components – the mast, rigging, foil arms and hydraulics – there are plenty of areas that each team’s designers have experimented with in the hope of giving their boat the race-winning edge.

Before he even picked his crew, Mr Sirena’s first job was finding the best design possible. Other bespoke technical considerations include the team’s clothing – isothermal, elastic, breathable and water-resistant gear designed by Prada in collaboration with Woolmark – and their watches – Panerai divers’ watches. The venerable luxury watchmaker is a sponsor and has created three commercially available versions of its Luminor diving watches, inspired by the materials and technologies in the Luna Rossa yacht.

“When we jump on board, everything is a tool related to performance,” Mr Sirena says, flashing his 47mm Panerai Submersible Luna Rossa. “Starting with the clothing: the shoes, wetsuit – and the watch is the same. It’s a partnership that builds on something real and specific. The case is carbon fibre, the dial uses the same cloth we are using on the sail. It’s a big watch, but it’s super light.” But there is one more factor. “The other important thing, the main thing,” Mr Sirena says: “It’s an Italian brand.”