She did her first Sydney to Hobart in 1984, now at 52, Adrienne Cahalan will become the first woman to reach a special milestone on Boxing Day.

He lives overseas, but Scallywag owner Seng Huang Lee grew up watching the Sydney to Hobart from close to the start line and wants to continue building the legacy set by his boat's previous owner, Syd Fischer.

Wild Oats XI reaffirmed its favouritism for this year's Sydney to Hobart with a dominant win in Tuesday's Big Boat Challenge.

Aaron Rowe will enter his maiden Sydney To Hobart alongside former Olympian Gavin Brady.

A Sydney sailor aims to be the first woman to solo circumnavigate Antarctica non-stop and unassisted.

Champion Australian sailor Jimmy Spithill has had some fine days on the water but this wasn't one of them as America's Cup holders Oracle crashed a test boat in Bermuda.

The two yachts involved in Saturday's tragic accident, which killed one man and left another in a critical condition fighting to keep his leg, hit head-on as one approached a mark off Clareville in Sydney's Pittwater, and the other began its run downwind.

The America's Cup next year is set to be the most competitive yet, believes James Spithill, the Australian skipper of the defending champions Oracle-Team USA.

James Spithill has built his reputation on fighting his way out of a corner.

• Sailing

A crew of predominantly Canberra-based sailors held their own in the demanding Sydney to Hobart yacht race.

Paul Clitheroe spent Wednesday night sweating on whether challengers would knock his 52-footer Balance off the top of the Sydney-to-Hobart handicap standings.

New South Wales boat Balance is the overall winner of the 2015 Sydney to Hobart yacht race.

After Syd Fischer declared that he will likely race the Sydney to Hobart for a 49th time next year after skippering his Ragamuffin 100 to second on line honours on Tuesday, his sailing master David Witt beamed and then quipped: "If he is stupid enough to keep going then I am."

Super-maxi Ragamuffin 100, owned and skippered by Syd Fischer, took second place on line honours in the Sydney to Hobart on Tuesday morning in a nail-biter of a finish with Rambler 88  – albeit an agonisingly slow nail-biter as winds virtually petered out.

Sydney to Hobart organisers should schedule a three day regatta of harbour racing before the Boxing Day start to provide foreign entries more value for their campaigns, says American George David, the owner and skipper of the US 88-footer Rambler 88.

Despite experiencing crippling fear, Erin Molan says she will give the Sydney to Hobart another crack after being forced to retire early.

American supermaxi Comanche has taken line honours in the Sydney to Hobart yacht race.

Darryl Hodgkinson can now say - no doubt with regret - that he has experienced the agony of the Sydney to Hobart to go with the ecstasy that came when he won the race on handicap in 2013.

When Syd Fischer and his maxi Ragamuffin 100 cross the finish line of the Sydney to Hobart yacht race as is expected on Tuesday, he will likely be greeted with the same cheer deserving of a winner.