Hard-bitten Sydney to Hobart race regulars have returned to dry land with stories of challenging conditions and some hard luck after more than a quarter of the fleet retired within the first 18 hours.

A full 24 hours into the race, Monaco's Black Jack was leading from fellow supermaxis LawConnect and SHK Scallywag as they battle off the Victorian coast, with a total of 62 boats still racing.

Eighteen boats pulled out on Sunday and a further eight followed on Monday morning as the conditions took a heavy toll.

The most prominent withdrawal on Monday was Alive, which won overall honours in 2018 and was fourth in 2019. The 66-foot Tasmanian yacht suffered hull damage and was heading back to Sydney.

Sailors returning to Sydney said it was heavy seas that caused most problems rather the southerly winds they were pushing into.

"The breeze was 33, 34 knots, which is not that bad," said No Limit crew member Declan Brennan, whose boat retired after one of the crew suffered a dislocated shoulder.

"Its curious, it wasn't angry conditions it was a just a very short, sharp seaway.

"The seaway was so inconsistent we were just bouncing around all over the place.

"This is a 63-foot boat. It just didn't make for a sensible thing to continue on."

South Australian John Willoughby, skipper of Enchantress, at least got nine hours into the race this year, having spent eight days in 2020 sailing from Adelaide to Sydney only to find the race had been cancelled minutes before he arrived.

His 2021 campaign was cut short after some spinnaker halyards came loose and knocked a hole in the mainsail.

It was part of a sequence of adverse events triggered by the boat being briefly plunged into darkness by an electrical fault.

As someone used to dealing with things going "pear-shaped" with a rudder falling off in three races and a mast going overboard in another three, septuagenarian Willoughby was too busy to get panicked.

"Thats what a Sydney Hobart does for you, it gives you the knowledge and the training to be able to get yourself out of any situation," Willoughby told AAP.

"But if we had gone on with that mainsail it would have just torn to pieces."

Tasmania's Cookson 50 Oskana, which won 2013 overall honours as Victoire, retired this year after breaking a headsail foil.

"We couldn't hold a headsail in that track and that was going to make it a really hard race if it's all upwind without a headsail, so we decided to retire, no major damage," Oskana skipper Michael Pritchard said.

"It's the coming down off the waves and landing is what shakes things out of the foils, so unfortunately it blew the foil out."

It was the first time in his four Hobart campaigns Pritchard failed to finish.

"The other Hobarts I've done have been quite a downhill run, this was a bit of a challenge," he said.

Cruising Yacht club of Australia commodore Noel Cornish explained the conditions.

"The southerly at up to 30 knots is not an unusual southerly for this sort of race," said Cornish.

"But the north travelling south current going against that 30-knot southerly is what has caused quite steep seas and that's what has done the damage.

"I think as the day progresses it's due to abate as a southerly front just moves through and moves up the coast."

© AAP 2021