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Wild ride

The Rolex Sydney Hobart Yacht Race serves up its usual beating, as a father and son from New York take on the classic contest for the first time.

The Rolex Sydney Hobart Yacht Race lived up to its reputation of a Christmas classic with a punch as staggering as any ocean sprint around.

A fleet of 87 boats started the race Dec. 26, and within two days 18 of them had retired.

"It was a tough race, no doubt about it, and one of the roughest I have been in," says Adrienne Cahalan, 45, co-navigator on Wild Oats XI, the first yacht to finish the 628-nautical-mile race from Sydney, Australia, to Hobart in Tasmania.

That says something. This was Cahalan's 19th Sydney Hobart, but she also has raced in the Whitbread and Volvo round-the-world races and on Steve Fossett's 125-foot catamaran Cheyenne when it set a circumnavigation speed record in 2004.

Within two days of the Dec. 26 start, 18 of 87 starters had retired from the race down the New South Wales coast, as three back-to-back "southerly busters" - frontal lines coming out of the south with stiff winds - met the fleet and the east Australia current head-on, says Roger "Clouds" Badham, dean of Sydney Hobart weather routers and Wild Oats XI's meteorologist. The collision of winds blowing up the coast with currents running south piles up tall, steep waves with deep troughs - huge potholes that can swallow a boat when it comes off a crest.

Badham reported winds of 25 to 40 knots over much of the course. Cahalan says the 100-foot maxiyacht Wild Oats XI powered through 12- to 15-foot seas in Bass Strait, a treacherous 150-mile-wide stretch of water between Australia and Tasmania that funnels currents and blasts of cold Southern Ocean wind from the Indian Ocean into the Pacific.

Loki, a Reichel-Pugh 63, finished strong.

Wild Oats XI's finish - in 2 days, 7 hours, 37 minutes, 20 seconds - was the fifth Sydney Hobart win for the maxi and its owner, Bob Oatley, a third-generation Australian with business interests ranging from vineyards, wineries and cattle stations to thoroughbred horses and an island resort near the Great Barrier Reef.

First-timers impressed

Yachts suffered rudder and sail damage and a dismasting. Wave Sweeper, a Beneteau First 40.7, dropped a crewman off in Eden with a broken ankle. Dawn Star, a Baltic 46 and one of two U.S. boats, was knocked down, throwing two crewmembers across the deck into white water sweeping over the lifelines. Both were wearing harnesses and life jackets that inflated as seas engulfed them and the boat - righting itself - scooped them back onto the deck.

A wave - big, square, breaking - had barreled into the sturdy racer/cruiser amidships in 45-knot winds and confused seas, says Will Hubbard, 26, who with his father, Bill, 69, had come halfway around the world to race in the 65-year-old sailing classic, their first. The New Yorkers were impressed.

"It lived up to its reputation, that's for sure," says Will, who spoke to Soundings by phone from Hobart.

"I can honestly say it was the worst race and the best race I've ever done - and that's the honest-to-God's truth," the elder Hubbard told reporters at race's end.

A weather briefing two days before the start gave the sailors fair warning of the conditions they would encounter.

Back in New York, he says, "The first one-and-a-half days of this race were a major nightmare." It was cold and bruising, and he was seasick most of the time. Then the wind and seas settled and the Baltic's speed picked up to 10 knots. "It was idyllic," he says. "The Sydney Hobart served up every kind of condition imaginable."

Will Hubbard, who sailed in his first Newport Bermuda Race when he was 16 years old and his first Fastnet when he was 17, set his sights on the Sydney Hobart after taking overall honors with his dad in the Newport Bermuda Centennial Race in 2006 aboard their vintage Carter 37, Lively Lady II. "I wanted to do the last of the major three" - the troika of offshore classics, he says.

Hubbard had been angling unsuccessfully for a crew berth on a Sydney Hobart maxiyacht since he was 18, and he finally decided, "If I have to bring my own boat across the ocean to do it, I'll do it," he says.

After two years of planning and another three years of hard work to raise money and prepare Lively Lady II, he was ready to race in the 2010 Sydney Hobart. It would be the grand finale to a cruise from Newport, R.I., through the Panama Canal and across the Pacific to Sydney.

"We planned [the race] around Will sailing around the world," says his mother, Robin, who gave her imprimatur to the whole idea on two conditions: Will would prepare the boat meticulously and equip it with all of the recommended safety gear, and when he got home he would write a book about the exploit.

Ominous cloud cover draped the fleet.

Two days before Will Hubbard and friend Brendan Shanahan's anticipated October 2009 departure from Newport, a nor'easter tore Lively Lady II off its mooring at the New York Yacht Club's Newport campus and pummeled it against a seawall. The boat was totaled. "That week in October was probably the most difficult in my entire life," Hubbard says.

A cruise, then the race

After absorbing the shock, Hubbard and Shanahan regrouped. They went on an emergency boat hunt, finding Dawn Star in San Diego in January 2010. It was a buyer's market, so the price was right, and Lively Lady's insurance money paid for it. They set off on the Baltic 46 the next month, stopping along the way at idyllic Pacific islands, where they took in the peace and the beauty and switched out friends and family as additional crew.

"It was the experience of a lifetime," says Hubbard, who deferred career plans and put his relationship with a girlfriend on ice to do it. "It's just amazing cruising. The pristine islands, the beaches, the tiny little villages with very rustic, wonderful people who treat you like family. ... I saw a side of life you can't see in New York."

He visited six countries and 50 islands in nine months, then raced the Sydney Hobart. Dawn Star finished 63rd, with 40 minutes subtracted from its time for chasing down a life raft to make sure there was no one in it, then sinking it. As it turned out, seas breaking on deck had swept the raft off one of the raceboats.

Hubbard says he'd do the race again. "I'd be up for another one, but I'm a glutton for punishment," he says. "For me, there's a little bit of unfinished business." He'd like to finish higher in the standings.

As the new year dawned, Hubbard was working as a sailmaker for the Quantum Sail Design Group in Sydney. His plans for 2011: race in the New York Yacht Club Transatlantic Race, the Transpac and the Fastnet. "I love racing offshore," he says.

At some point he will make his way across the Indian Ocean, around the Cape of Good Hope and on to the United States or Europe.

Cahalan says she has been through some rough Sydney Hobarts - the 1984 race, the 2000 race, when she faced 60-knot winds in Storm Bay. The Sydney Hobart gained international notoriety in 1998 when a low-pressure system developed over the northeast Bass Strait and raked the fleet with winds gusting to 80 knots. The vicious storm claimed six lives and sank five boats, forced the retirement of 66 others in the 115-boat fleet, and precipitated a massive rescue operation that plucked 55 sailors from the water.

Line honors went to Wild Oats XI - (from left) skipper Mark Richards, co-navigator Adrienne Cahalan and Patrick Boutellier of Rolex Australia.

In the wake of that disaster, the Cruising Yacht Club of Australia adopted measures requiring more crew experience and training, as well as safety and communications gear and crew attendance at race and weather briefings.

Bill Hubbard, who at 69 says he, too, would do another Sydney Hobart, says it's a race every devoted ocean racer has on his or her bucket list. "It's like climbing K2, I guess," he says.

This article originally appeared in the March 2011 issue.