With the yachts starting on handicap times, the Sydney Amateur Sailing Club hopes this will result in a spectacular mass finish, under spinnaker before a fresh seabreeze.
The fleet comprises gaff-rigged and Bermudan rigged wooden boats, the majority on the register of the Sydney Amateurs, which conducts regular racing for these classic yachts, along with entries from other clubs.
Coming down from Pittwater for the Sydney Harbour Bridge 75th Anniversary Regatta is one of the oldest yachts still racing in Australia, the 27 foot gaff-rigged yawl Killala, believed to have been built in the mid to late 1890s.
Beautifully restored by shipwright Ian THOMAS for owner Mitchell GALBRAITH, Killala will be helmed on Sunday by Hugh TREHARNE, the tactician on Australia II in her America's Cup victory in 1983.
Also built in the 1890s is the 28 foot gaff cutter Jenny Wren, owned by Neville OLLISSE.
Two classic Bermudan rigged oldtimers, Ben STONER's Weene and Martin COX's Gannett, will be racing against other for the first time since 1911 when they both competed on Hobart's River Derwent.
Not only are the yachts of veteran age. Bill GALE, now in his early 80s, will be at the helm of his famous gaff-rigger Ranger, which he has helmed or crewed for the past 60 plus years. Ranger carries the SASC sail number A1.
Biggest boat in the fleet will be Nigel STOKE's Fidelis, the 66 footer that took line honours in the 1966 Sydney Hobart Race and raced to Hobart again last December to celebrate the 40th anniversary of that victory.
Another famous former ocean racing yacht competing is David CHAMPTALOUP's Caprice of Huon which twice represented Australia at the Admiral's Cup in England in the 1960s.
Clean Up Australia founder Ian KIERNAN's Maris is another former ocean racer competing while prominent political advisor Ian KORTLANG will be helming his classic metre boat Antara.
The classic yachts, which will race in three divisions, Spinnaker, Non-Spinnaker Division A and Non-Spinnaker Division B, will be joined by a fleet of Historic Skiffs, replicas of the gaff-rigged 17 footers that raced on Sydney Harbour before the Bridge was built.
Among the Historic Skiff skippers will be Irish international yachtsman Harold CUDMORE, a past America's Cup and Admiral's Cup skipper, who will be helming The Mistake.
Unlike the SASC club sail numbers or Yachting NSW sail numbers carried by the yachts, the Historic Skiffs will be distinguished by colourful emblems on their mainsails, the same as those carried by the original boats of that name.
For example, Alruth's emblem is a A in Shield, Australia IV carries a Union Jack on its mainsail.
The Sydney Harbour Bridge 75th Anniversary Regatta race will start at 13:00 from a line northeast of Clark Island, racing down the Harbour to the Beashel Buoy, then back to round the Shark Island mark before heading up the Harbour to a rounding buoy west of Fort Denison.
From there the course will take the fleet back to round Shark Island, then up the Harbour again, passing the Fort Denison buoy to starboard before finishing between the Committee boat Captain Amora and the bark Endeavour.
The prizegiving will be held later on Sunday afternoon at the SASC clubhouse in Mosman Bay, with many of the competing boats expected to berth there after the race.
A full list of entries, along with the course, is available from the Sydney Amateur Sailing Club website - www.sasc.com.au.
The SASC is conducting the Sydney Harbour Bridge 75th Anniversary Regatta on behalf of the NSW Premier's Department, Office of Protocol and Special Events.