Wild Oats XI won the race out of Sydney Harbor Monday in the 67th Sydney-to-Hobart and started surfing down the east coast on a cyclone-generated swell and tailwind, but the 88-yacht fleet will be hit by a gale-force southerly headwind during the night. Favorite maxis Wild Oats XI and Investec Loyal engaged in a tacking duel to the heads, with Australian supermaxi Wild Oats XI suffering a series of gear problems related to power outages and was forced at one stage to give way to its rival. But as Wild Oats XI cleared the harbor it had opened up a comfortable three boat-length lead and hoisted its spinnaker and started powering south in the 628 nautical mile race. Hugo Boss, a hi-tech, water-ballasted 60 foot downwind flyer from Britain, played it safe and took its time to sail out of the heads, ensuring there was no chance of any incidents in the crowded start line. “There will be some fantastic speed set by the maxis down the coast,” said Cruising Yacht Club of Australia (CYCA) Commodore Garry Linacre. “They will probably get 100 nautical miles under their belt before the change comes in, which is almost one-sixth of the race over, in just a few hours,” Linacre said. “Record-breaking speed but then the breeze will come the other way with that traditional southerly buster type weather. We've heard up to 40 knots gusts. That will be very interesting and test the fleet but I'm sure they are all ready for it.” Southerly headwinds were forecast to prevail through Tuesday, before easing in the later stages of the race. “It's going to be tough – 30 knots on the nose is tough in anyone's books,” said Ed Psaltis, co-owner of fancied handicap contender AFR Midnight Rambler. Wild Oats XI is aiming for its sixth line honors victory, but given the southerly storm the race's record of 1 day, 18 hours and 40 minutes is not in jeopardy. “A southerly on the first night will sort a bit of the fleet out,” Wild Oats Xi skipper Mark Richards said. “We'll hopefully get through that first night in one piece. It's going to be very light at the other end of the race, so it will be very tricky.”