Boats on trucks, Rolex watches and replicas of 260-year-old cannons: Inside the Sydney to Hobart

The Rolex Sydney to Hobart is one of the most prestigious yacht races in the world, with hundreds of sailors descending on Sydney Harbour each year to race for the Tattersall Cup. Starting in 1945 with just nine boats, the race has swelled to host 104 competitors this year.

To unpack some of the quirkier features of the race, this masthead went to the Cruising Yacht Club of Australia, the host of the annual race, and asked Commodore Sam Haynes to explain it all.

What does it take to qualify?

Before arriving at one of the four starting lines in Sydney Harbour, boats and their crews must qualify. For sailors, the rules state that all competitors must be over the age of 18, with at least half of the crew having sailed competitively on larger vessels, and the entire crew on smaller ones. Sailors can be both amateurs and seasoned professionals.

Boats must have a single hull, and measure between nine and 30 metres in length. They must also have competed in a recognised qualifying race of no less than 150 nautical miles at least six months before the Sydney to Hobart.

How do boats get to race day?

Crews travel from far and wide. The furthest travelling yacht this year is Cocody, a French vessel that covered 15,000 nautical miles to arrive in Sydney. However, many boats are shipped to Sydney to protect them from wild open ocean conditions.

Commodore Sam Haynes will be the first sailing commodore in recent memory, aboard Celestial V70.Credit: Flavio Brancaleone

“When you take the wear and tear, the risk, and the insurance [into account], it’s safer and more reasonable to ship boats on container ships,” Haynes said. “We’ve had boats that have been on trucks from Western Australia ... that can happen also.”

How is traffic managed in Sydney Harbour?

Boxing Day is one of Sydney Harbour’s three busiest days (alongside Australia Day and New Year’s Eve), and if the weather is nice, the water can resemble a traffic jam. Competing yachts, support boats, media vessels, and spectators fill the harbour. It takes a fleet of official boats to keep everything in check.

Traffic on the water is managed by NSW Maritime and water police.

The public, aboard everything from one-person kayaks to well-stocked commercial vessels, are kept in an “exclusion zone” that keeps everyone safe, and Haynes said anyone who crossed the line would “find out pretty quickly”. Harbour ferries are halted for the beginning of the race.

How do the boats know when to go?

Competitors mostly rely on the CYCA countdown being streamed onto their vessels and the hoisting of special flags. But to keep the tradition alive, replica cannons from Captain Cook’s Endeavour are fired at 12.50pm, 12.55pm and 1pm (when the race actually starts).

This year’s cannon firers are seasoned sailor and overall race winner Simon Kurts, two-time line honours champion George Snow and long-time sailor John Winning snr.

Though it may seem counterintuitive, racing to be the first over the line once the cannon is fired can prove a risky pursuit because crossing the line early incurs penalties that could cost competitive boats the race.

Haynes, who will race this year aboard Celestial V70, said: “In a lot of racing, you’ll push the line to be on it as close as possible but in the Hobart race because it’s such a long race, you want to be safe. So part of the tactics is just to make sure you’re not over the line [early].”

Master Lock Comanche is expected to contend for line honours.Credit: Getty Images

What is a protest?

As with any sport, there is a lengthy list of do’s and don’ts, and the Racing Rules of Sailing dictate the spirit of the competition. Racers are required to help those in danger and demonstrate sportsmanship and fair play. They’re also required to give each other space, not hit turning marks and give right of way based on orientation.

Penalties for breaking the rules can include additional minutes being added to one’s finishing time, or a boat being forced to make 360-degree turns in the water.

“Protests have to be given immediately, directly from one boat to another, so that they know that they can go through a process where they can exonerate themselves,” Haynes said. “Even if they feel that they’re in the right, they can still do penalty turns, and that would mean that they can then exonerate themselves.”

What do the winners take home?

Despite the magnitude of the 628-nautical mile race, the prizes for the Sydney to Hobart are humble. The two most high-profile awards are the Tattersall Cup — for fastest adjusted time after handicap — and the John H. Illingworth Challenge Cup — for fastest over the finish line at Hobart. Both prizes come with a Rolex watch. Prizes are also given out for individual divisions, including the first female skipper over the line, the first small boat to finish, and more.

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