Darlinghurst

A four-level extravaganza with a retro cocktail bar with views over Hyde Park, stone-baked pizzas, and a Japanese menu by an ex-Sake chef.

Dimitri’s first started as a lo-fi little pizzeria on Crown street; in 2019, it moved up to Oxford Street. The new digs feature an Italian-made woodfire oven, a bigger dining room, plus a dedicated small bar upstairs. The toppings here are a riff on Dimitri’s flavour-over-tradition approach.

Here, it's all about the mozzarella.

This is the godfather of Italian dining in Sydney. Beppi’s has been ticking-over with the same consistency, fit-out and leather-bound menus – hand-carved by the late Beppi Polese himself – since 1956. Immortal dishes include clams and mussels with garlic, olive oil, white vino and tomato; and zucchini flowers stuffed with ricotta, basil and mushrooms.

A shop that sells inventive sourdough-brioche doughnuts by a classically trained pastry chef. Traditional flavours are playfully twisted here – there’s a Vegemite-spiked salted butterscotch and another filled with Basque cheesecake.

This takeaway-focused old-school sandwich shop makes some of Sydney’s best (and biggest) sangas. But you don’t need to take our word for it – the lengthy queues that form outside it every single weekday at lunchtime should tell you how good these sandwiches are.

This is where Bill Granger first became Australia’s unofficial brunch ambassador. At one time, this breakfasts at this sun-drenched cafe were the yardstick by which all the city’s cafes were measured: avocado on Iggy’s bread, poached eggs with elevated sides and ricotta hotcakes. A blond-wooded, white-walled institution.

A tiny Darlinghurst cafe with a unique riff on Japan’s most convenient sandwich: the pork-katsu sando. Here, it’s staked with salted cucumbers, pickled carrots, nori and American cheese. Best of all, it’s cheap. Expect “sort of poke” bowls and Single O coffee too.

Enter this extravagant cafe in a corner art deco building – featuring a striking Keeley Baird (from Something More Design) fit-out and a mural by artist Andrew Dennis – for truffles, caviar and a toastie that has to be seen to be believed.

Italian that starts with a boozy breakfast.

The successor to Chippendale's Freda's channels the spirit of the original late-night haunt into a buzzing sit-down bar and diner in the heart of Sydney's nightlife district.

Italian food, drinks and hip-hop served until 3am. Yes. Big Poppa's is low-key one of Sydney's best places for cheese-lovers – whether you like it on a platter or inventively deployed across a range of pasta dishes.

An intimate vibe and 300-strong wine list make this one a date-night home run.

Drink, dance, shoot pool and snack on Eastern Europe’s finest.

A Miami Vice themed bar with an appropriately tropical cocktail menu to match.

When Rivareno's Darlinghurst location opened, it was the first non-European outpost for this renowned Italian gelati chain. And though it's since spread across Sydney, we think that this one's still the best.

Wall-to-wall books on design make this one of Sydney’s true specialists of the genre. You can find back issues of high-end mags such as Monocle and Creative Review, but that’s not all – there’s also a raft of merchandise for sale by witty design crew, Good Fucking Design Advice.

An essential part of Sydney’s LGBTQI history. Visit for a comprehensive range of literature, magazines, DVDs, erotica and some very sexy calendars.

This colourful store sits on the CBD end of Oxford street, with enough variety to give designers, artists and literary types plenty of inspiration (or procrastination).

This is Sydney's most popular gelato shop, and it's not even close. But it's well deserved adulation: even though it's since become one of Australia's best-known gelato brands; the flavours, the quality of ingredients and the exacting attention to detail have, if anything, improved over the years.

It stocks 150 plant varieties – the majority of which are indoor and shade-friendly. And if you’re lacking a green thumb, it’ll help you keep your new purchases thriving.