Hamilton Island itself could be described as Australia’s Nantucket—were Nantucket owned by a single family.

After making a fortune founding Rosemount Wines (sold in 2001 for AU$1.1 billion), flamboyant 87 year-old Bob “Popeye” Oatley bought the island, a lush green dot 16 nautical miles off the northeast coast of Queensland in the Whitsunday archipelago, for AU$110 million 10 years ago. The family then poured an additional AU$400 million into upgrading its facilities. The jewel in the crown is the Qualia resort, a Relais & Chateaux property that opened in 2008 on the island's northern tip. There, 60 plush teak-and-glass pavilions are accessed via a Jurassic Park-like electric gate: discreet stone, steel, and teak set in impassable jungle. (About two-thirds of the island remains wilderness.) Its Beach House bungalow, said to be Oprah's favorite, with private pool and the best view of the regatta, went for AU$2,900 a night during race week.

Audi may put AU$1.3 million ($950,000) into its annual sponsorship, but the Oakley family puts in a lot of personal funds as well. Despite the island giving itself over to the week—package holiday resorts, conference centers, six high-rise apartment rentals, all booked—the Oatleys told me the race was essentially a loss leader to attract media attention while indulging their own sailing passion. (Surprise, it has worked.) 

Truly Arriving

To get here is simple: You can take a 30-minute ferry, book daily flights from around the country, or fly privately, as many locals do. During race week, the one-runway airport showed private planes lined up like minivans at a suburban mall.

Arriving is another thing. As a journalist on a two-hour commercial jet from Sydney, I saw plenty of boisterous glamor. Coiffed socialites mingled with posh-accented sailors in the open aisles at the back of a Virgin Australia plane, plotting, socializing, and flirting. (No air marshals here, mate!) At one point, a small fashion show erupted from one the rear lavatories. “Too much?” a twentysomething asked as she emerged from the starboard head. “Naaaw, shows off your admirable rear,” said one of the blokes. “McQueen,” the girl said smugly, name checking the designer. It was a mile-high Anna Karenina, with a 737 substituting for the ballet theater.

What would the island’s original inhabitants, the Ngaro Aboriginal people, have said to all this hubbub? They navigated these islands in three-piece bark outrigger canoes, snagging green sea turtles, coral trout, and parrotfish with bone-tipped spears. After at least six millennia in the area, all they left behind are ochre paintings of marine life in some sea caves. Today, members of a distant tribe—Kylie Minogue and Johnny Depp, who was filming the latest Pirates of the Caribbean sequel nearby earlier this year—ride golf carts along the old hunting paths. 

A Whale of a Time

The races take place amid a maze of the 74 pine-covered and mountainous Whitsunday Islands, named by Captain Cook in 1770 as he sailed through them on Britain's Whitsunday holiday. Last week, the yachts shared the waters with the vanguard of some 20,000 humpback whales migrating north toward warmer waters. Crew members were frantically pulling iPhones from waterproof jackets to shoot cetacean mothers and calves doing sudden ballet leaps out of the water among the boats.

“The mother whales won’t eat for the entire three-month journey, so they can keep their full attention on the calves,” Sandy Oatley told me aboard his yacht. (His father, the sail week's traditional king, was missing due to a knee injury.)