Restaurants

  • In the former home of Paddington institution Lucio’s, this homey diner carries on its predecessor’s legacy with classic Italian dishes, non-traditional pastas and a selection of mainly Italian wines.

  • Buzzing Bootleg Italian does “bootleg” plant-based versions of Italian classics. The whole menu – from fluffy dough balls with garlic butter to cacio e pepe and lasagne – is vegan. Don’t forget to order a serve of incredibly convincing tiramisu.

  • This backstreet local made a particular name for itself under Colin Fassnidge's culinary leadership but is now under new management. It retains its produce-driven menu but without the nose-to-tail ideas Fassnidge was keen on. There's a bigger wine selection than most pubs and taps pour all of the classics.

  • An unassuming terrace house on the outside; a fun Latin American bar and diner on the inside. Dishes span Peruvian, Mexican and Brazilian flavours, backed up by a solid selection of tequila and mezcal. The best drink on the menu? The Tequila Mockingbird, of course.

  • A wood-fired oven, an open-flame hearth and some of the country’s best produce and cocktail bar underneath.

  • The old-school Italian with the iconic green door has been kicking hard since 1987 with honest Napoli-style fare including hand-made pastas, fish and beautifully prepared meat courses. The tablecloths are white, the upholstery is floral and the service is pitch-perfect.

Cafes

  • At the Melbourne-born roaster’s first Sydney shop, you’ll find seasonal espresso blends and single origins alongside excellent pastries and bread. Plus, everything you need to lift your coffee game at home – from hand-grinders to espresso machines and beyond.

  • Breakfast and lunch from the much-loved bakery.

  • This bustling, pretty cafe fuses traditional Italian flavours with local brunch staples

  • There are giant cookies, à la Scout's Honour.

  • A young team dishes up breakfast until five at Five Ways.

  • This Paddington bookseller does food, drinks and books. And what a combination that is. Every book across its three levels is second-hand, with regular bargains to be had. The website is constantly updating, with titles landing daily – even if they’re used, the rotation keeps things feeling new.

Bars

  • An all-star cast has been assembled for this vinyl-spinning bar: P&V's Mike Bennie is on wine duty, Maybe Sammy is handling cocktails, and star chef Clayton Wells is doing food. The highlights? A fried-potato dish and BYOR (that’s bring-your-own-records) nights.

  • The team behind Maybe Sammy have moved into a heritage Paddington pub and created a Mexican-inspired bar all about good times. There’s a DJ booth, disco ball and a menu that riffs on classic Mexican dishes. Cocktails are a big yes given who’s behind the place.

  • Set over two storeys in an iconic Paddington terrace, Sydney’s most experimental wine bar has Italian swagger in spades. Come for pastas that are anything but traditional, and a pretzel with whipped bottarga that’s so spectacular it’s never left the menu. The wine list changes so frequently, you could visit three times in a week and never get bored.

  • Like end-to-end diner Fred’s upstairs, this warm basement bar employs the best of the season’s produce on a menu that truly has something for everyone. Fancy something fresh and lively? Sure thing. Or perhaps a stiff, old-school classic? Right this way.

  • Like a cross between a pub, a bistro and chicken shop. Enjoy the rotisserie-focused menu in this sleek and sunny fit-out. If you've got a solid amount of pals for an event, ask for the private space, a magnificent frieze-covered dining room with a sun roof.

  • This classic English pub was founded in 1875. There are little Union Jack flags on the table and a menu that lists everything from fish and chips to dhal. It's a classic family pub, filled with dogs, daily specials and match-day Swans supporters.

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Shops

  • Stonewashed linens, crisp cottons and beautiful accessories, designed right here in Sydney.

  • Josh Niland – of the boundary pushing seafood restaurant Saint Peter – is behind this retail seafood boutique.

  • Another instalment for the cult bottle shop. Swing past to pick up a bottle of skin-contact chardonnay or a slab of Heaps Normal non-alcholic beer. Or snag a seat in the courtyard out back for by-the-glass-wine and terrine by ex-Old Fitz chef Nicholas Hill.

  • So much more than the average high-street jeweller.

  • The crown jewel of the Berkelouw empire in Sydney. This three-storey literary landmark on Oxford Street has everything a book nerd could wish for, not least of all a good cup of coffee from the upstairs cafe. It’s licensed and open late, which means it’s primed for a pre-movie drink if you’re hitting the Verona Palace Cinema next door.

  • Like the classic takeaway joint, but with more technique.