As the fleet headed into the first night, Comanche, eight-time champion Wild Oats XI, Black Jack and Infotrack were vying for the lead with another rival, Hong Kong's Scallywag, an early withdrawal from the 85-strong field with a broken bowsprit.
The traditional Boxing Day start for the 74th staging of the classic ocean race saw thousands of spectators lining Sydney Harbor as the yachts sailed away in perfect conditions with 10-15 knot north easterly winds.
Peter Harburg's Black Jack was first out of the Sydney Heads, with Comanche, skippered by owner Jim Cooney, initially trailing before showing its paces as the 100-footers reached speeds of 30 knots.
Comanche, billed as the fastest monohull yacht in the world after setting a string of records, won last year's race in a record time of one day, nine hours, 15 minutes and 24 seconds, but the outcome was mired in controversy.
Perennial winner Wild Oats XI was first into the Tasmanian capital of Hobart by 26 minutes, but was handed a one-hour penalty by an international jury after a near-collision with its main rival near the start.
With lighter winds forecast than last year, the record for the 628 nautical miles race is expected to stay intact with the tactical moves in the Bass Strait between the Australian mainland at Tasmania likely to hold the key to victory.
"The real issue is linking all the bits of wind up," Wild Oats strategist Iain Murray told reporters before the start.
"I think the boats that keep continuously moving fast (will benefit)... the difference between going fast is going five knots, or 10 knots or 12 knots and if you do that for a couple of hours it is a big difference," he added.
Aside from the battle to be first into Hobart, other entrants will be eying victory in the various divisions for different type of boats and overall handicap honors, the entrant that does best when size is taken into account.
Renowned owner-skipper Matt Allen won with 52-footer Ichi Ban last year and was bidding become the first competitor in 54 years to secure back-to-back victories.
Allen was also wary of the tricky sailing conditions. "It's a real tactician's strategy race," he told reporters Wednesday.
The annual race has been contested since 1945 and has the reputation of being one of the most testing yacht races on the international calendar, with conditions in the Bass Strait particularly challenging.
Tragedy struck in 1998 when six competitors lost their life in a fatal storm with only 44 finishers in Hobart from 115 starters.
Thursday will see crews mark the 20th anniversary with a moment of silence on race radio to commemorate the fallen and the reading of a message of tribute.
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