It was Perpetual Loyal that made the sweetest start under northerly breezes of up to 20 knots.
It was also first through the heads in last year's race and its crew will be hoping for better fortune this time, having been forced to retire in 2015, as they were the year before.
Wild Oats XI skipper Mark Richards was caught swearing on the live coverage amid what he freely admitted was "a terrible start".
Pinned on one side of the course, he had to tack back and thread the needle through a cluster of smaller boats that got the jump on his bigger yacht.
CQS, Ludde Ingvall's radical 100-footer, appeared to suffer a keel problem and lost considerable ground as it tilted steeply to one side.
Following Perpetual Loyal through the heads was the 80-foot Beau Geste, then Scallywag and Wild Oats XI.
But Wild Oats XI had moved into third by the first mark and went on to reel in the leaders as the fleet headed south down the NSW coast.
The four supermaxis were expecting to sail mostly in favourable northerlies, though there is a southerly change forecast.
"The record will get broken," Scallywag skipper David Witt predicted. "Our routing has got one day 11 hours to the Iron Pot, that's seven hours inside the record and with about 12 miles to sail."
Wild Oats XI set the existing record of one day 18 hours 23 minutes 12 seconds in 2012.
"I think it does look optimistic for a race record," Wild Oats XI tactician Iain Murray said. "The breeze is kind, there's a lot of northerly quadrant wind.
"The race record is not actually that fast, it's 17 knots average or something like that. We averaged 21 knots in the Brisbane-to-Keppel race earlier in the year."
The race's first casualty, Freyja, built in 1945, damaged her headsail shortly after going through the Heads.
"We didn't really have much propulsion, not adequate, we decided to turn around," skipper Richard Lees said.
Asked how he thought the damage happened, Lees said: "We probably had too big a sail up. I'm fairly fatalistic but some of the others are more disappointed than me."
Simplesail Mahligai, an Australian-based boat representing Russia, was last out of the heads. It broke a sail batten but opted to carry on.
Charlotte protested against Triton, but there were no immediate details.
- AAP