Painstakingly crafted to replicate the sailing workboats that graced Sydney Harbour and Parramatta River in the 1880s, the 10-foot skiffs look stunning, complete with polished timber hulls.

But with their massive surface area of sails mainsail, jib, and spinnaker to relatively small hull, "the little buggers buck you off like a horse," Gillespie said.

In his maiden racing season, the Teralba club member capsized, and was disqualified, in four consecutive races.

"I nearly had a for-sale sign on the boat, I can tell you," the 60-year-old recalled.

Only an "over-inflated sense of humour" and the adrenaline rush of racing under full sail motivated him to persist.

Yet, despite his humbling beginnings, Gillespie has become a NSW title-holder, taking handicap honours in the Australian Historic Sailing Skiff Association 10-Foot State Championship last year.

On Saturday and Sunday he and his crew aboard "Ramona II" will start their title defence when South Lakes Amateur Sailing Club at Sunshine hosts the first two races of the four-leg championship.

The Sunshine regatta will create some history of its own as the first time the titles have ever been held outside of Sydney.

The event will also mark the inaugural Lake Macquarie Historic 10-Foot Skiff Championship.

Gillespie and his crew of two others won last year with a handicap of 10 minutes, which is deducted from the overall time to form the handicap placing.

But that benefit has been cut to five minutes this year, so Gillespie tips past winner John Lewis's entry "Keriki" (off 10 minutes) to claim handicap honours.

"If we were a racehorse we'd probably be carrying too much weight," he said.

South Lakes club stalwart Pete "Alfie" Jacobson has built a boat, "Miss Marlene".

His son Dale Jacobson, along with Dale's wife Tracey and Alfie's son-in-law John Hodda, will race it in the titles, which will end with two races next weekend at Drummoyne.