Charlie Vowell is looking to recreate history during the Variety Bash next month.
Mr Vowell, his brother Richard, cousins Brett and Robert Pollock and his wife's cousin Tim Hough will be cruising during the event in A-model Fords.
"We have a 1928 model Ford utility with a wooden tray and a 1930 sedan model A Ford Phaeton," he said.
Mr Vowell said he wanted to relive the experience of his aunt, who was the first person to drive across the Sydney Harbour Bridge in 1931.
Mr Vowell and his team Big Kids Helping Kids hope to raise $20,000.