“In time this will be the northern equivalent of the Sydney to Hobart race,” Bourke says. “It will become the iconic ocean race north, just 550 nautical miles [1018 kilometres], but with much more pleasant water temperatures.”

A large number of entries – more than the 230 boats which took part last year – is expected for Race Week 2019, including the elite craft that are sailing’s equivalent of motor racing’s Formula One.

Other sailing regattas race around buoys. At Hamilton, we race around islands.

— Glenn Bourke, Hamilton Island chief executive

Hong Kong department store baron Karl Kwok, for example, has brought his record-breaking trimaran Beau Geste to compete against Hooligan, owned by longtime Financial Review rich lister Marcus Blackmore (who, with a personal fortune of $463 million, narrowly missed the 2019 Rich List’s $472 million cut-off).

Meanwhile, the Oatley family’s Wild Oats X – famously raced in December by the first all-female professional crew to take part in the Rolex Sydney Hobart Yacht Race – will be banking on “home advantage” in the Whitsundays.

It’s now 16 years since the late Bob Oatley (entrepreneur, wine maker, philanthropist and highly competitive sailor) persuaded his family (No. 87 on the 2019 Rich List) to buy what was then a failing island resort that happened to have a great sailing carnival.

Bestselling author Rob Mundle, doyen of Australian sailing journalists, was on board a predecessor of Wild Oats XI after the 2003 Race Week. According to Mundle, Oatley called his two sons – Sandy and Ian – on deck for a family confab.

Hamilton Island – developed by another Australian business visionary, Keith Williams, in the 1980s – had fallen on tough times. Its Race Week, held for the first time in 1984, had sunk in terms of entries and prestige. Now the island was up for sale again.

To quote The Castle, Oatley’s sons told him he was dreamin’. But Oatley insisted they run the prospectus past the company’s chief financial officer, Phil Costa.

“The Oatleys had to have their bid in by the end of the week,” Mundle recalls. “Phil threw the documents into his bin, saying: ‘Bob, we know about wines, and we know about coffee. But we know nothing about running resorts.’

“But Bob said, ‘Just take it home and look at it, Phil. Tell us what you think tomorrow.’

Hamilton Island has made this more than a sailing event: it’s a social and cultural happening.

— Tom Ehman, US sailing veteran and editor of Sailing Illustrated

“The next morning Bob and the boys were in their offices when Phil walked in. He was wearing a straw hat, a floral shirt and shorts. And he said, ‘Bob, it’s a deal!’ ”

Since then the Oatley family have spent more than $500 million redeveloping Hamilton Island. The adults-only, six-star qualia resort (with its private beach, fine dining restaurants, spa treatments and exquisite views of the Whitsundays from 60 exclusive “pavilions”) accounted for at least a fifth of that.

Then came the island’s signature yacht club (another $85 million, including the luxury villas next door).

Plus the 18-hole championship golf course, which in November will once again host the finale of the Australian PGA (another $45 million, although to be honest the hilly course is actually on neighbouring Dent Island – a five-minute ferry from Hamilton Island Marina.)

Bourke’s life has been spent sailing competitively in the Caribbean, the Mediterranean and the Pacific, but he had never experienced Race Week until 2008, when Oatley chose him as the island’s new chief executive.

So how does he rate it?

“The scenery of the Whitsundays and the waters around Hamilton Island are at least equal to anywhere else in the world,” he says.

The biggest change since the first Race Week has been the vast increase in the number of women sailors.

“Other sailing regattas race around buoys. At Hamilton, we race around islands. That’s technically demanding but aesthetically beautiful. It’s a luxury to have 74 islands in the Whitsundays, so we can set the courses each morning for the wind conditions. That makes for quality racing.”

Naturally, in the 35 years since the inaugural Hamilton Island regatta, there have been changes. The races used to be much longer, stretching into twilight. But today’s yacht crews prefer shorter, sharper races – sometimes two in a day.

The biggest change since the first Race Week, however, has been the vast increase in the number of women sailors. “Back in the day, sailing was a predominately male sport,” Bourke says. “Now it’s not far off 50-50.”

Bob Oatley’s genius in transforming Hamilton Island Race Week was converting a mainly macho escape into a female and family-friendly event.

Oatley introduced fashion parades – and an egalitarian mix for those who want to enjoy the nightly entertainment with a beer and a takeaway from one of the pop-up food stalls on Front Street.

And then there’s “lay day”, the Wednesday of each Race Week – a throwback to a more genteel age of sailing.

Instead of racing, the crews take the day off. That might mean catching up with family, heading off to Whitehaven Beach, enjoying the traditional Pool Party with old mates, or accompanying a non-sailing partner to the signature Charles Heidsieck champagne lunch at qualia.

During this Race Week, Hamilton Island will have an occupancy rate of about 95 per cent. Forty per cent of visitors will be from NSW, with another 20 per cent each from Victoria and Queensland, plus 10 per cent from abroad.

Legendary America’s Cup identity Tom Ehman describes Race Week as “the best kept secret in yachting” and recommended organisers of other major regattas “look at how Hamilton Island has made this more than a sailing event: it’s a social and cultural happening”.

Oatley died in 2016, aged 87, but there is no statue marking his contribution on Hamilton Island.

“Bob wouldn’t have wanted one,” Mundle says. “Race Week is his memorial.”

Bourke concurs. “There have been a lot of friendships and memories built at Race Week over time: many grand old stories and a few lies told over a couple of beers. Bob changed the whole persona of Hamilton Island and Race Week.

“He turned it into somewhere you could have the most elegant meal, cooked by Australia’s finest chefs, with matching wines. Or a place to enjoy a sausage sizzle with a few too many rum and cokes after a great day’s sailing.

“This is his legacy.”

Race Week at a glance

When | Saturday, August 17 to Saturday, August 24
Starts | Usually between 10.30 and 11.30 am, in front of Hamilton Island Yacht Club
Race classes | Four classes for racing boats (IRC, One Design, Performance and Racing Multihulls), plus four for cruising boats (IRC Passage, Cruising, Non-spinnaker and Cruising Multihulls)
Lay day | Wednesday, August 23. Hamilton Island offers more than 60 activities, from game fishing and bush trekking to koala cuddling and spa treatments.
Dress code | Smart casual (for shore activities).
Accommodation | Hundreds of competitors sleep on their cruising yachts in the marina. Others opt for the luxury of qualia, the renovated Beach Club, more economic alternatives like the four-star Reef Hotel, or one of the 160 private holiday homes on the island available for hire.
Best spectator spots | Hamilton Island Yacht Club, or Quantum (the official spectator boat). Several companies offer spectator charters – including for sailors who want to crew while watching the action.
What else | August is a perfect time to watch humpback whales on their annual migration between Queensland and Antarctica.