Wollongong yachtsman Derek Sheppard is a veteran of six Sydney-to-Hobart campaigns but this year's race will be a new experience.
It will be his first as a boat owner after he acquired Black Sheep, formerly Honeysuckle, with brother Martin in April with the specific intention of tackling the blue water classic.
"The first one I did on Stormy Petrel and I've done five Hobarts with St Jude but we've bought our own boat this year with the sole intention of racing it in the Sydney-Hobart," Sheppard said. "My brother and I have both had other boats so the crew is a mix of people from those boats and a few who actually came with the boat, so it's a good, experienced crew."
Since they bought the boat in April, the new owners have overseen an impressive campaign in the CYCA Blue Water Pointscore with a 16th-place finish in the Sydney-to-Gold Coast Yacht Race, eighth in their division, a third-place finish in the Flinders Islet Race in September and a fifth in October's Bird Island Race.
Most recently they raced the 45-footer to 11th place in November's Cabbage Tree Island Race.
Sheppard is confident the preparation leaves his crew well equipped ahead of the Boxing Day start.
"It's been pretty good, everything's been going well," Sheppard said.
"We had a good Sydney-Gold Coast race and we had a CYC trophy regatta last weekend - we got third there so that's pretty reasonable [preparation]."
Though confident his crew can arrive in Hobart in under four days, Sheppard said early forecasts indicate favourable conditions for the maxi yachts like six-time defending champion Wild Oats XI.
"The gods determine the weather window and that says whether it's going to be a big-boat race, a middle-size boat or a small-boat race," Sheppard said.
"At the moment it's looking like a big-boat race or, if not the big boats, the 50 to 60 footers."
Sheppard said strong winds forecast off Tasmania's coast on day three of the race will make it tough for smaller boats.
"The current forecast is looking like reasonably hard running conditions down to Victoria, a mixed bag across Bass Strait and strong to gale force winds down the Tasmanian coast," he said.
"The gurus are saying that the first day is pretty sorted and the last day is pretty sorted but the middle's very unknown at this stage.
"There's a quite complex trough system that develops in the middle of the race.
"Currently the meteorologists are saying that the earliest you can know about that is when you're actually there.
"That's going to make it tough for the smaller boats."