The Illawarra Marine Rescue unit has had to pull in "10 or 12" damaged Sydney to Hobart yachts in recent years.
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The supermaxis and the hobbyists sailboats have set off from Sydney harbour to the cheers of thousands assembled in person and countless more watching on television, but Bruce Mitchell will be keeping a closer eye on the race than most.
Mr Mitchell, regional co-ordinator for Marine Rescue Illawarra, said his crews will monitor the fleet as it approaches the Illawarra and sets sail for Tasmania, with rescue crews prepared to head out and render assistance to stricken boats at a moment's notice.
"We're on standby if required. If one of the yachts gets into trouble, we go out and get them," Mr Mitchell said.
"Once they get a bit further down, the Ulladulla boat will be going out."
American yacht Comanche has taken the early race lead. The fleet is expected to encounter rough seas between Kiama and Jervis Bay, and strong winds between Sydney and Kiama.
Mr Mitchell said the area south of Port Kembla was usually the source of trouble for yachts sailing down the Illawarra coastline, with bad weather and equipment failure common.
"They leave Sydney all fine, but we've had to help out boats with broken gear or broken masts, ones that have lost steering," he said.
"We've probably had to pull in 10 or 12 boats over the last 10 years."
Mr Mitchell said his crews would monitor radio and respond in case of emergency, but said a "mothership" following the fleet to Hobart would be able to deal with minor issues.
"Fingers crossed, we won't need to do anything," he said.