The Rocks eats differently by day and by night — follow the clock and the day stacks up in layers.
Lunch and afternoon
Lunch at Circular Quay or a harbour-view restaurant, then a drink at one of the oldest pubs (like the Fortune of War) in the afternoon is the classic order Fact. The MCA café is also a good light stop with harbour views.
Down into the night
There's a layer here for whisky and cocktail lovers too. The Doss House is a whisky bar set in an 1840s sandstone cellar, Maybe Sammy is a globally recognized cocktail bar, and Frank Mac's is known for its gin collection Fact.
A suggested order
Lunch at Circular Quay or a harbour-view restaurant, afternoon drink at an oldest pub, dinner at the market or a steakhouse, and a nightcap at a sandstone cellar bar — following this order keeps the day's texture intact. Check individual venues' hours and menus just before you go.