The dockworkers who historically plied their trade in this inner-east precinct of Sydney would summon some salty language to describe the current toffy inhabitants. (A Hollywood actor! A row of fine-dining establishments! Air-kissing cocktail drinkers!) Sorry, fellas, but when a neighbourhood is this appealing, gentrification is going to happen. Less than two kilometres east of the Sydney CBD, with the Domain on one side and ritzy Potts Point on the other, Woolloomooloo was always ripe for restoration. But the suburb isn’t all water and fine wine. Head inland and while the bars get hipper and the bakeries more artisanal, you’ll still find pubs sticking resolutely to how they were way back when.

The Amalfi Way

The Amalfi Way

Italian waiters with oodles of personality. Sweeping city views. And exquisite pastas, pizzas and antipasti. Restaurateur Luigi Esposito’s The Amalfi Way seems to cover all the bases. But perhaps the biggest tick is the sense of la dolce vita the restaurant creates right in the middle of Sydney. Occupying a prime spot on Woolloomooloo’s famed Cowper Wharf, the Italian eatery is an excellent spot for revelrous dining with a side of unapologetic people-watching. Kick off the night with a serve of Guazzetto Di Mare Freddo – an entrée of beautifully cooked octopus, calamari, scampi, mussels and prawn, literally swimming in a pool of parsley and butter. Follow it up with a pizza laden with smoked ham, mushrooms, marinated artichokes and black olives, and a dessert of sponge cake soaked in lemon cream. Just don’t forget to pair it all with a bottle of the crisp and light Falanghina from Campania from the expansive wine list.
Shop 2/6 Cowper Wharf Roadway, Woolloomooloo; (02) 8367 5834


Alibi, Sydney

The pull of the Ovolo Woolloomooloo’s on-site, plant-based eatery Alibi is magnetic. Designer Hassell Studio has woven pockets of intimate dining and drinking space among the millennial pink and blonde wood accents to cultivate a cosy restaurant within a vast, sonorous venue. The attitude of the place is homey but there’s an sense of adventure evident in the menu. Dumplings are cleverly crafted from coconut flesh and the udon noodle bowl, bejeweled with mushrooms, warms and comforts in its slurpy, creamy (yet certainly-not-cream-based) mess.
6 Cowper Wharf Roadway, Woolloomooloo; (02) 9331 9088


Otto, Sydney

Special occasions often find their way to Otto, a beloved osteria overlooking the Finger Wharf’s bobbing boats. Offerings are technically surf and turf but with notable nuances of regional Italian technique – pane carasau, gnocco fritto and under-appreciated pasta shapes such as strozzapreti (hand-rolled tubes) – that reveal its subtle genius. This simplicity has kept Otto atop the list of Sydney favourites for almost 20 years – and will continue to do so, if the saffron bucatini festooned with Moreton Bay bugs is any indication.
Area 8, 6 Cowper Wharf Road, Woolloomooloo; (02) 9368 7488


There are two types of visitors to Woolloomooloo Wharf:  those who want to see where Russell Crowe lives; and those who want to dine well in a precinct that showcases Sydney’s style. The latter crowd tends to gravitate to Manta, where the menu leans heavily on delicious seafood and service that’s relaxed and refined at the same time. Split a plate of fried Loligo calamari with black garlic aioli, pickled fennel, chilli salt and mâche, then go solo with sourdough-crumbed King George whiting or oven-roasted Cone Bay barra. Not into seafood? Not a problem. The beef is presented with just as much love and is sourced from 100 per cent grass-fed cattle on restaurant-owner Rob Rubis’s Queensland farm. Snag a waterside table (they’re all undercover), order a cocktail and a selection of oysters – the regions change daily – and watch the sky turn lolly pink as the sun sets behind what’s about to become a sparkly city skyline. Then raise your glass. You’ve hit peak Sydney.

6 Cowper Wharf Road; (02) 9332 3822

The Tilbury Hotel

The Tilbury Hotel

Across the road and a short stroll from the flash wharf, The Tilbury manages a perfunctory nod to the gritty past while embracing the light, bright, open-plan present. A clever layout caters to just about any pub-goer’s whim, whether it’s bending an elbow in the front bar, clinking frosty glasses of rosé  in the sunny courtyard or dropping onto an upstairs sofa with a book and a glass of red. The airy restaurant – a breezy blend of blonde wood and taupe – spills out to the courtyard via wide glass doors. Kick off a sunny Sunday lunch with dishes such as beetroot-cured kingfish or chargrilled octopus tentacle, then follow up with king prawns, Moroccan-spiced lamb leg or miso-glazed eggplant. Think you’re finished? You still have to try the frozen mango parfait with caramelised rum banana and coconut sorbet.
12-18 Nicholson Street; (02) 9368 1955

Flour and Stone

Eschewing the tasteless visual perfection that seems to prevail in pastry thanks to the Instagram era, this rustic bakery makes cakes how you remember them from childhood. Only your Mum likely never whipped up pannacotta-soaked lamingtons or fig-dotted brown butter cake. Order a slab of one of the bakery’s most indulgent triumphs (Valrhona Manjari Chocolate, anyone?) and devour in between sips of coffee. You’ve never been closer to heaven.
53 Riley Street, Woolloomooloo; 8068 8818

Contact Bar and Kitchen

Flour and Stone lamington

It’s a thoroughly modern dilemma: if you don’t snap a photo of your perfectly plated meal, did you even really go out for dinner? Well, at Woolloomooloo’s Contact Bar & Kitchen you don’t have the choice. You have to rely on your five senses to lock down the memory of the melt-on-your-fork Bangalow pork because your smartphone gets locked away behind the bar upon entry. Though the tech sacrifice is optional, it’s all part of the fun in this unassuming space, decorated with rotary dial telephones in a cheeky nod to what you’ve given up. Boost the intrigue levels even further by ordering the $49 four-course secret degustation menu, which could include highlights from the broadly European menu such as wafer-thin beef carpaccio and creamy tiramisu – but who knows?
88 Crown Street; (02) 8318 1510 - Kate Barracosa

Stay: Ovolo Woolloomooloo

The cavernous setting of this hotel right on the 100-year-old Finger Wharf may demand a jacket in winter months but everything else at this Sydney stay radiates pure warmth. Ovolo Woolloomooloo is hospitable at every turn: it’s in the complimentary goodie bags on your bed that insist you ask for refills and the fully stocked mini-bar that’s yours for the ransacking. It’s in the free happy hour drinks enjoyed among retro gaming consoles and cosy couches in the central bar. Most discernibly though, it’s in the engaging art and temptingly tactile furniture that populates each room. Everything is practically begging to be snapped for Instagram.
6 Cowper Wharf Roadway, Woolloomooloo; (02) 9331 9000

This piece was originally published in 2018 and has been updated.

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SEE ALSO: The Best New Bars in Sydney

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