Somewhere along the 628 nautical-mile journey from Sydney to Hobart, retired naval officer Bob Williams will lay a sailing legend to rest, and fulfil a promise that brings a tear to his eye.
The promise traces its origin to the turn of the century, when Williams was re-fitting his new boat Sylph VI on the NSW mid-north coast.
Williams had bought the 41-foot cruiser in Townsville in 1997 with the idea of sailing her around the world - a lifelong goal that had helped inspire him to join the navy more than 20 years earlier.
"I was looking for a long-distance cruising boat, that was my focus," Williams told AAP.
"It's a bit basic for modern standards but she proved to be a really great boat for single-handing and ocean sailing."
As Williams worked away on his new toy, a man walked up the marina and placed his hand on Sylph's bow pulpit. He turned to Williams and said: "I haven't touched this boat in 17 years".
That man was David Lawson, a Sydney to Hobart veteran and one of the sailors who helped build Sylph forty years earlier.
Lawson's father Jim and his brothers Archie and Mick owned Sylph when she sailed the bluewater classic for the first time in 1961 with fellow Hobart debutant David on board.
On Marchioness, Lawson contested his 33rd and last Hobart in 1998, when six lives and five boats were lost amid torrential weather conditions.
The man affectionately nicknamed 'Lawso' died in 2016 and as his last wish, he asked his sailing buddies to meet for drinks at the Cruising Yacht Club of Australia in lieu of a funeral service.
After learning Sylph would be sailing in the Hobart for the first time since 1972, Lawson's son Brett contacted Williams with another request.
"He has asked me to scatter his father's ashes on the way down to Hobart," Williams said.
"There's that connection over a couple of generations, with the boat's original owners.
"I feel very pleased to be able to do that for Brett."
Williams has sailed Sylph around the world two-and-a-half times, into the icy waters of the Arctic Circle, around each of the great capes and across the most remote sections of the Pacific Ocean.
But even a man of his worldliness becomes emotional talking about the promise he will fulfil in the days after Christmas.
"It is one of my motivations, it's not so much about me," Williams said.
"It's about the boat's history and her heritage and keeping that going, and hoping that when my time with her comes to an end, that someone else will be inspired to keep that legend going.
"That would be really great."
Sylph is the oldest boat in a fleet that has 103 entrants as of December 21.
She's one of 18 boats entered into the relatively new two-handed division, but Williams says it's unlikely a boat of her vintage could win that.
As he considers his multi-million dollar race rivals, though, the Hobart debutant is not at all fazed.
"I just want to show any ordinary person can do it if they set their mind to it," he said.
