Perched on the Finger Wharf, this long-lunch fave is officially one of the city’s best steak restaurants. It also flaunts an iconic waterfront location to go with its premium steaks and crustaceans.

Thai-food legend David Thompson’s right-hand woman is behind this seductive eatery. From the theatrical open kitchen, she’s celebrating the nuances and beauty of Thai cuisine, with flavour-punching dishes you might not find anywhere else in Sydney.

A wine bar with an ever-changing menu inspired by southern Italy.

Woolloomooloo’s 150-year-old nautical-themed pub.

Sleek and informal Asian dining at the Cowper Street Wharf. The menu is a knock-out homage to the best of Chinese and south-east Asian cuisines. Try tenured dishes such as tea-smoked duck with tamarind and plum, or the pork belly with chilli caramel and nam pla phrik (sweet-and-sour sauce). White tablecloths and city skylines included.

Halfway down Woollomooloo’s picturesque Finger Wharf, Otto has been celebrating la dolce vita for more than 20 years. Also, seasonal produce in the form of modern Italian dishes – best enjoyed from the seats that spill out onto the wharf overlooking the sparkling harbour.

To call it a mere bookshop would sell this place short. Vintage threads and a sizeable record collection are some of the other treasures you’ll find here. It also hosts gigs, writer’s talks and long-table dinners. Grand nights indeed.

Soaring ceilings and vast wall displays usher in a new chapter in the florist’s story.

Hot pies until 4am.

If there’s such a thing as home-baking heaven, this supply store by the Flour and Stone team might well be it. High-grade flour, rare butter and other baking essentials are in abundance. Plus cookbooks, pavlova kits and Nadine Ingram's famous plum pudding.

Nadine Ingram is one of the city’s master bakers, and this compact spot is where all her magic happens. Head here for gorgeous cakes, salads and sandwiches to take away. For baking supplies, cookbooks and more, hit the pantry a couple of doors up.

A florist and patisserie in one in Woolloomooloo.

Named for the Earl who made sandwiches popular, John Montagu is putting lots of thought between two slices of bread.

Woolloomooloo’s great-grandfather of a pub has fine-dining chefs in the kitchen and a celebrated indie theatre downstairs. The 150-year-old boozer has outlasted many of its operators, but its latest incarnation – from the team behind Newtown's Odd Culture – might be the best one yet.

Where the drinks are vibrant and people talk about the flux capacitor.

Busby is a decadent cocktail and function room, and your next nightcap destination.

Firstfdraft is a multipurpose gallery, studio and office on Riley Street in Woolloomooloo.