Is it really too much to ask? One – will only fly business or first class. Two – must always travel with a bespoke Louis Vuitton case. Three – at all times should be accompanied by a minimum of two armed guards.

You’d be forgiven for thinking this is the rider of some A-list celebrity, but the only diva here is a trophy – for this is just a small sample of the list of demands that go along with the highly prestigious, and precious, America’s Cup.

Dating back to 1851, the cup – originally called the £100 Cup (though mistakenly engraved as the 100 Guineas Cup upon instruction from the American winning team), predates the modern Olympics and is said to be the oldest trophy in international sport. And, though it perhaps represents America’s longest winning streak in any sport (the New York Yacht Club held the cup for an eyebrow-raising 132 years, from 1851 until it was finally taken from them by the Royal Perth Yacht Club in 1983), it doesn’t take its name from the country, but from the first ever vessel to win the cup – The America – witnessed by Queen Victoria at the 53-nautical-mile race around the Isle of Wight. It won against 15 other yachts.

But today the numbers of contestants are even fewer – the $3m entry fee has something to do with that. And that’s not taking into account the cost of the craft (around $8m-$10m per boat) and the crew that you’ll need to sail past the finishing line.

This is the sport for the world’s 1%. People like Larry Ellison, co-founder of American software giant Oracle, who, in 2013, reportedly poured $115m into Oracle’s Team to successfully defend their America’s Cup title.

But with the recent change in the rules to allow smaller vessels (48ft instead of 62ft) to take part, there are signs that the organisation is trying to open its doors a little wider. Though there is some controversy around this move – with Luna Rossa, sponsored by fashion house Prada, pulling out in protest – 2017’s 35th America’s Cup will see six teams compete in first-time-host Bermuda.

Take Warhol’s ‘Flowers’, for instance. I’m told MOMA has one of these prints. Here, you’ll find nine.

If you’re confused as to why there’s only been a total of 35 competitions in a 166-year history, let me explain: there is no regular schedule for this competition (clearly). It rallies round only when a qualifying yacht club challenges the club that currently holds the cup. So this can, and has, and probably will continue to, take years between shots.

Because it’s not just the cost, but the effort involved that you have to consider. Boats have to be built from scratch – and it’s not just the one you’ll need but, as of this time round, at least three. The official boat of the race, plus a couple of training catamarans for good measure – much like those you might have seen in the Extreme Sailing Series.

And, with that in mind, the official Bermudian host – The Hamilton Princess & Beach Club – has just undergone a $100m refurbishment, including the first and only full-service marina in the whole of Bermuda. With 60 berths, accommodating yachts up to 150m in length, it offers access to the likes of the ocean-loving super rich, people like Ellison, which they haven’t had before.

As we take a considerably more understated boat out to try some local snorkelling, Swedish team Artemis are already here to test the waters. Their catamaran skims smoothly back and forth across the ocean alongside us. It’s like ballet on water – elegant, streamlined and seemingly effortless.

But as lucky as I feel to catch a sneak peek at what’s to come, I have some of my own demands from this ocean-side resort. First up, I want my own piece of the action.

You name it, I’ll try it. At their private beach club – a pleasant 15-minute ride from the hotel – I paddleboard for the first time in the calmness of their enclosed waters. Balancing, I find, is not the problem, but working out the technique of using a single oar – do I switch hands or not? Who knows. I wing it and enjoy it, before grabbing a canoe and heading out of the bay. A mistake, because once in open waters turning around to make the journey back was trickier than I had an anticipated, but part of the challenge.

For a rather more efficient tour of the island, opt for the two-hour jet ski safari. We travelled all around the island, taking in the landscape, the recognisable white roofs of the houses designed to catch and recycle rainwater (which is required by law on the island), the world’s smallest drawbridge named after the county I was born in (Somerset), a shipwreck, and turtles who are accompanied by schools of iridescent fish.

When it comes to beauty, the Hamilton goes more than nature-deep – it’s blessed with some rather amazing contemporary art, too. Its collection – which is curated and owned by the Green family, who also own the hotel – is unlike any other you may see in your entire lifetime. It certainly gives the Dolder Grand in Zurich a run for its money.

Take Warhol’s ‘Flowers’, for instance. I’m told MOMA has one of these prints. Here, you’ll find nine. And there’s a lot more where they came from, perhaps because he was a personal friend of the Greens’ late mother. I’m even told they have a Warhol of her, but this is one of the few pieces they choose to keep private at their family residence – which is on the island across from the hotel.

But that’s just the tip of a rather large iceberg – a giant blue-mirrored piece, entitled ‘Monkey (Blue)’ by Jeff Koons sits in the lobby, to its side more Warhols – a string of his ‘Camouflage’ prints – offset with a row of Yoshimoto Nara on the opposing wall, an unmistakable Hirst spot painting to their right, and underneath sits a Banksy.

Mondrian, Lichtenstein, Invader, Hockney, Mr Brainwash, Ai Weiwei, even art by Nelson Mandela – if I was to list all the artists behind the 100+ artworks around this incredible hotel, I’d run out of column inches. But perhaps one of the surprise pieces for me (aside from the Mandela) is the 30ft sculpture by New York-based artist KAWS. A clown-like figure, based on Mickey Mouse, with his face obscured by both hands towers over you as you tuck into breakfast outside the Princess’s Crown and Anchor restaurant, or sip on bubbles in the evening at the Veuve Clicquot bar.

Like the hotel’s art, the food is something to note. Especially in Marcus’ – named after the chef, Marcus Samuelsson, the man also behind the infamous Red Rooster in Harlem. The fish chowder bites and deviled eggs are worth the trip to the island alone.

But my favourite spot of all – sans artwork – is definitely the infinity pool, where the lines between you, the pool and the ocean blur into one. And that’s at the top of my rider – cracking views of the most successful sailor in Olympic history, Ben Ainslie, captaining his four-man crew to take the title from the Americans and bring the America’s Cup back home to Britain, where it all began in 1852.

For more info, thehamiltonprincess.com