What exactly is the measure of what makes a place cool? Ratio of commercial to craft beer? The length of a barista’s beard? Kale consumption per capita? Whichever metric is being used, these seven slices of Sydney simply ooze cool. From the golden sands of Bondi to the black coffee of Surry Hills, welcome to the Harbour City’s most stylish suburbs.
A huge city split by a sparkling harbour, Sydney is divided into a string of distinct enclaves. The grungy breweries of Marrickville have a totally different vibe to Balmain’s chic boutiques, and sultry CBD speakeasies feel miles away from Bondi’s brilliant beach.
Camperdown Memorial Rest Park is just one sprawling green space in a city famed for its harbour and imposing skyscrapers | © Alana Dimou / Culture Trip
This is all part of the city’s magic, reckons Sydney nightlife kingpin Mark Gerber. “Not only from a topographical, geographical standpoint, with obviously the most incredible harbours in the world,” Gerber says, “but all the different precincts that come together, making for an incredible global city.”
Sitting on Central Station’s doorstep, the 2010 postcode was a deeply working-class area until inner-city professionals arrived in the neighbourhood. Surry Hills has swapped seedy for small bars and speciality coffee, thanks to cafés like Paramount Coffee Project, Reuben Hills and Single O, plus cutting-edge restaurants such as Chin Chin, NOMAD and Firedoor.
Surry Hills, Sydney’s central suburb, is the home of speciality coffee | © Alana Dimou / Culture Trip
Gentrification hasn’t entirely bleached out the rough-and-tumble roots of Surry Hills, though – this suburb still contains the highest concentration of quality watering holes in the Harbour City. Grab a schooner of Resch’s at pubs like the Shakespeare Hotel, The Forresters and the newly renovated Keg & Brew hotel for a taste of old-school Sydney.
McElhone Place, also known as Cat Alley, is a tranquil sidestreet in Surry Hills | © Alana Dimou / Culture Trip
“I love our eclectic mix of customers and sense of community,” says Em Smith from the Shakespeare Hotel. “It doesn’t matter who you are or where you’re from, if you’re nice you’ll always make friends at ‘the Shakey’.”
Paramount House Hotel offers spectacular views | © Alana Dimou / Culture Trip
Sydney’s most bohemian borough is the gateway to the inner west, the most fashionable part of the city. And King Street is Newtown’s street art-caked spine, lined with independent retailers and offbeat boutiques that are just as eclectic as the residents themselves. Old classics such as Clem’s Chicken Shop share the strip with vegan joints like Lentil As Anything, with record stores, bookshops, vintage boutiques and a bevvy of bars in between.
Bohemian enclave Newtown is the gateway to Sydney’s inner west | © Alana Dimou / Culture Trip
Home to a huge student population belonging to Sydney University next door, Newtown also boasts plenty of places that are Sydney’s ‘best something’. Mary’s fries Sydney’s best burgers. The Enmore is Sydney’s premier gig venue. Young Henry’s is Sydney’s favourite brewery. The Courthouse Hotel – simply ‘the Courty’ to locals – is arguably Sydney’s top beer garden.
In Newtown, old classics are squeezed between newly opened eateries and boutiques | © Alana Dimou / Culture Trip
“Having been born in Newtown, I have seen many changes over the years,” says Baz Scott, owner of the beloved Egg Records. “We love the neighbourhood as it’s never boring. There’s always something that you will see and that will amaze you, make you smile, make your day. I hope it stays that way.”
Surry Hills’ next-door neighbour evolved from a similarly gritty suburb into the heart of Sydney’s LGBTQ community. Darlinghurst, defined by its rainbow-coloured Oxford Street precinct, hosts Sydney’s epic Mardi Gras celebration every March, and keeps the party going 12 months a year.
A string of boutique galleries – Stanley Street Gallery, The ARTERY Aboriginal Art Gallery, King Street Gallery, Arthouse Gallery and Gallery 9, to name a few – ramp up the cool factor, as do late-night haunts like Shady Pines Saloon and queer club ARQ. And Darlinghurst will only get cooler with the news that the government has relaxed the lockout laws that crippled Sydney’s after-dark economy between 2014 and 2019.
Owner of Darlinghurst nightclub Oxford Art Factory, Mark Gerber, says: “The area’s nightlife scene has been on an incredible journey of exploration, discovery, vibrancy and freedom of expression, especially on the Oxford Street strip, giving the LGBTQ community the opportunity to put themselves firmly on the map.”
Bondi might be a little more upscale than the other places on this list, but its biggest drawcard doesn’t cost a cent. Bondi Beach is perhaps the most famous stretch of coast on the planet, and the streets sloping down the sand are brimming with salubrious bars, boutiques and cafés where visitors can grab a kale smoothie or breakfast bowl with the activewear-clad locals.
The Bondi Icebergs Pool is one of the suburb’s main attraction and is completely free | © Alana Dimou / Culture Trip
When they’re not sunning themselves on the beach, Bondi’s glamorous residents splash their cash at waterfront restaurants like Sean’s Panorama or the Icebergs, with its dining room towering above the area’s Instagram-famous ocean pool. The views from the Bondi to Coogee walk – a stroll along the clifftop via Tamarama, Bronte, Gordon’s Bay and Clovelly – are just as dazzling, especially in October when the Sculpture by the Sea exhibition takes place.
Bondi Beach is encircled by trendy eateries and is the starting point for the beautiful Bondi to Coogee walk | © Alana Dimou / Culture Trip
“Bondi is all about the beach,” says Craig Wachholz from Let’s Go Surfing, a surf school and training centre. “You’re in the middle of a cosmopolitan city of five million people, but when you get into the water for a surf or swim, you feel like you’re a million miles away.”
Like most suburbs on this list, Balmain had a long blue-collar history – the Australian Labor Party was founded here in 1891 – before it became one of Sydney’s most salubrious postcodes in the new millennium. This harbourside patch of the inner west is a web of leafy streets lined with historic terraces, all jostling for a view over the water.
The big Italian community infuses Balmain with a Mediterranean flavour – the cafés and restaurants along Darling Street are testament to that. And while the neighbourhood’s many pubs would have been filled with grizzled wharfies or dockworkers a century ago, swanky venues such as The Balmain Hotel, Wilhelmina’s and the East Village Hotel are now well populated by fashionable young professionals.
“Balmain is a community of small shops and locals that support us,” says Samara Golding-Piper from Wilhelmina’s, which occupies a grand Victorian building that began life as the local Working Men’s Institute. “I personally love getting to know people that come through the doors. Wilhelmina’s is a place for family and friends.”
The Balmain’s Leah Hartley continues: “We love Balmain for its quirky houses, village vibe and array of quality pubs and eateries all within walking distance”
The thousands of commuters that flood Sydney’s central business district Monday to Friday aren’t particularly cool. But the sheer volume of world-class bars and restaurants that sit beneath their offices certainly are. The centre of Sydney is naturally the centre of Sydney’s culinary scene, and the CBD buzzes with life long after the lawyers and bankers have caught their trains home in the evening.
The Baxter Inn is a fixture on the coveted World’s 50 Best Bars list, headlining a crop of cocktail joints, including Bulletin Place, The Lobo Plantation and the Ramblin’ Rascal, beneath the skyscrapers. Restaurants like Quay and Bennelong either side of Circular Quay, plus Hubert, Tetsuya’s, Aria, Long Chim and Mr Wong lead a never-ending list of top-quality eateries, which Firedoor owner-chef Lennox Hastie insists have caught up with Sydney’s arch-rival, Melbourne.
“Sydney was previously leading the forefront from a fine dining capacity over many years, and Melbourne always had a lot wider variety in terms of the European offering but also the accessible price point,” Hastie says. “But now Sydney’s taken that on board and it’s got a lot more to offer at all levels. It’s given Melbourne a pretty good run for its money in the last few years.”
This industrial-chic quarter of the inner west has become more chic than industrial in recent years. Working-class Marrickville welcomed large groups of Greek immigrants post World War II then Vietnamese refugees a couple of decades later, and those flavours are imbued in the great-value diners along Illawarra Road.
Coffee and craft beer are the staples of Marrickville | © Alana Dimou / Culture Trip
Coffee and craft beer are the staples of this hipster-heavy neighbourhood today thanks to cafés like Coffee Alchemy, Two Chaps and Matinee, plus breweries such as Batch, Grifter and Willie the Boatman. Local brews aren’t hard to find in character-packed pubs like the sun-kissed Marrickville Bowlo, the dog-friendly Vic on the Park and The Henson – a winter favourite with rugby league fans en route to the hallowed Henson Park to watch the Newtown Jets, Sydney’s quintessential sporting experience.
It’s all about culture, industry, community and dog parks in Marrickville | © Alana Dimou / Culture Trip
“It’s a beautiful mix of culture, industry and community, and from that you get some really great people and things happening in the area,” says Andrew Fineran from the Batch brewery. “I live in the area as well, and there’s always something interesting and inspiring happening. I’m proud to live and work in Marrickville.”
Batch is run by a Marrickville local | © Alana Dimou / Culture Trip