The 18 Footers is partly a harbourside restaurant and mostly a harbourside bar. It is also strewn with reminders of the Winning family’s long history of sailing. John Winning senior is the club president and boats sailed by the family are memorialised in black-and-white photographs around the room.

This is where I meet John Winning jnr, better known as Herman, who on Boxing Day will skipper Andoo Comanche out of Sydney Harbour and down to Hobart. Last year, under Winning, Comanche won the Sydney to Hobart.