Discover Sydney’s city gems to eat, drink and play

Sydney’s inner city suburbs are your ultimate playground for late-night activity, dining and entertainment
Stanley Street alfresco dining
Photograph: Supplied
By Melissa Woodley for Time Out in association with Department of Enterprise, Investment and Trade (Office of the 24-Hour Economy Commissioner)
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Summer is the ultimate time to step outside your local neighbourhood and discover a secret side of Sydney. The city and its surrounds light up with al fresco activities, cheerful happy hours and after-dark performances that will carry you through to the early hours of the next day. Uncover your next adventure or visit a restaurant you’ve never been to before with our guide to the city’s underrated gems for dining, drinking and entertainment. Read on to discover what’s happening in YCK Laneways, Paddo Collective and Stanley Street.

These precincts are supported by Uptown – a program helping local business communities enhance their districts into vibrant going-out hubs. 

Eat, drink and play in the city

If you want to immerse yourself in the buzzing late-night scene of the CBD then YCK Laneways is your new best friend. Clock off work and unwind with a drink at one of YCK’s legendary bars including Papa Gede’s for happy hour from 4-6pm on Monday through to Saturday; relax under the fairy lights at SILY with free live music every Thursday in May through their Live on The Garden Stage series; enjoy $12 signature cocktails and $9 tacos during happy hour at Esteban; swing down to the Swinging Cat for live jazz and a night cap; or head to PS40 for its Takeover Tuesdays series featuring weekly guest chefs from some of the best restaurants in Sydney. Discover all the venues to plan your night using the YCK Laneways map here.

Paddo Collective

Paddington, or ‘Paddo’ as it is lovingly known, is home to some of the top-tier restaurants and most legendary watering holes in Sydney, making it easy for you to dine and unwind every day of the week. Step into the local scene and join The Paddington every Sunday for Sunday Roast and $12 Bloody Mary’s; hit up Saint Cloche’s new exhibition from proud Wiradjuri woman and self-taught artist Hannah Lange; or raise a glass to bottomless lunch at Tequila Mockingbird every weekend. During weekdays, you can score $12 snacks and cocktails during Tequila Mockingbird’s happy hour from 4.30-6pm; or take over DJ duties at Playlist Thursdays at Paddo Inn. For an extra something special, visit Fred’s for an epic collaboration between London chef Max Coen (Dorian in Notting Hill) and Fred’s executive chef, Ben Greeno from May 26 to May 29. After a few tipples, head to  The Unicorn for free parties and DJs, every Friday from 9pm to 3am. Discover more of what Paddo has to offer on the Paddo Collective website.

Stanley Street

Coffee and bottomless breakfast, DJs and dancing – Stanley Street really does have it all. You can stay and play from the early hours of the morning to well after dark with evening activities on offer all down the road. Stanley Street once held the title of Sydney’s Little Italy and maintains the cheerful charm of days bygone. Drop by Sydney institution Bill and Toni’s for home style Italian with a side of celebrity spotting, Harry’s by Giuls for bottomless brunch, Bar Nina for bottomless anytime (seriously, even breakfast), The Lord Robert’s for happy hour on Monday to Saturday from 3-5pm, and the Long Goodbye for a classic or bespoke cocktail using house-made liqueurs. Find top class Mexican at La Farmacia or for the brave, Wings N Tins have a doom juice wing challenge which you can wash down with a selection of over 60 craft beers. Enjoy mouthwatering authentic Mongolian BBQ at Wooden or the late-night menu at Japanese Yorimichi which runs until midnight.

The Uptown program is a NSW Government initiative being delivered by the Office of the 24-Hour Economy Commissioner.

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