Whenever I hear travellers in Sydney ask the question ‘What do you think of Sydney?’ I can’t help but cringe a little. Sydney is made up of so many diverse stories and people, each staking their claim over different neighbourhoods around our ever-growing city. It’s so easy for visitors who drop by to miss the best of what we have to offer.

If you’re wondering where to go in Sydney after you’ve seen its main attractions, I’ve compiled a list of suburbs as a starting guide to sampling our Sydney’s coolest offerings.

Top 10 Coolest Neighbourhoods in Sydney
image by Jason James via flickr

1) Surry Hills

Nestled in the suburban part of Sydney, Surry Hills is infamous for housing the misfits and the uber-cool in Sydney’s hip food scene.

By day, locals know it as a creative hub where many of Sydney’s biggest media companies work. By night, you’ll see the crowd moving to the other side of the suburb. For first-timers, the first thing you’ll probably notice is that Surry Hills doesn’t come with big glaring signs. The parties move underground here, and food strips are daringly close to the quieter, residential terraces. The people in Surry Hills relish in the understated.

Music-buffs who cringe at chart-hitting tracks, head down to Play Bar (my favourite) for a taste of local artists and DJ’s busting out in soulful lyrics and hiphop beats every night of the week.

Top 10 Coolest Neighbourhoods in Sydney | Surry Hills
image by Felipe Neves via flickr

2) Newtown

Newtown has long reigned as Sydney’s most recognised alternative hub, the beating heart of our bohemian arts scene. Just a train stop away from the city, this suburb is easily explored by walking down its long-winding main street, King Street.

Dotted with a dozen local art galleries and street art murals, it’s no wonder a vibrant crowd of unorthodox artists and musicians have made Newtown their permanent home.

Top 10 Coolest Neighbourhoods in Sydney | Newtown
image by Newtown graffiti via flickr

3) Bondi Beach

When it comes to snagging the title of Sydney’s most famous beach, the famous shores of Bondi wins every time. These golden sands are the backdrop of countless celebrity appearances and even a popular TV show, so much so that locals hardly even bat an eye when they’re spotted surfing Bondi’s breaking waves.

Bondi is one of the most accessible beaches from the city, with buses passing through and dropping passengers right next to the coastline every couple of minutes. As a perfect break from the city, the beach neighbours a strip of classy restaurants that pair a quality dining experience with fantastic beachfront views.

For the less gastronomically inclined, the beach is cluttered with premium gelato stores. There’s nothing more satisfying than grabbing a huge serving of ice cream to enjoy on the sand – though you’ll be surprised at how fast the ice cream melts!

Top 10 Coolest Neighbourhoods in Sydney | Bondi Beach
image by Andy5855 via flickr

4) Manly Beach

Bondi is an awesome summer hangout if you don’t shy away from a noisy crowd and love to socialise. For anyone looking for a quieter alternative, Manly Beach is the perfect candidate. You’ll often see locals making their way to Manly via the public ferry, riding from the shores of the inner city right across to the other side of Sydney.

Once you’ve docked onto Manly’s shores, there is much to check out – a great thing to do for nature-lovers is to make the trek to North Head, one of Sydney’s best whale-watching spots. The walk to these sandstone cliffs will also score you uninhibited views of the inner city.

Hang around once the sun sets and you’ll see Manly’s vibrant nightlife make a laidback appearance. With a far stronger touch of the local compared to Bondi, Manly’s beachside strip is somewhat smaller yet more welcoming, dotted with live music venues that cumulates in the annual Manly Jazz event where artists bring their trumpets out as they march through the beach and play for the entire neighbourhood.

Top 10 Coolest Neighbourhoods in Sydney | Manly Beach
image by Kim via flickr

5) Darlinghurst

Darlinghurst has a chequered reputation throughout history with a tumultuous past carved out of crime, sex and drugs. In recent years, Darlo has completely reinvented itself as the flamboyant corner of Sydney’s inner city. Nowadays, just a stone’s throw away from Sydney’s congested city area, this neighbourhood is best known for the annual Mardi Gras parades that trawl through Oxford St.

On every other night of the year, it’s the backdrop of an eccentric bar scene, where the madman retreats from his 9-5 work life. Those who drop by swap their casual wind-down over beer for crazy cocktails, shameless dancers and the spirit of partying way too late on a weekday.

A favourite retreat of mine is Hinky Dinks, a tiki-themed retro bar mixed with the unapologetic enthusiasm of the 50s cocktail culture. As the people there put it themselves – cocktails first, questions later.

Top 10 Coolest Neighbourhoods in Sydney | Darlinghurst image credit: Sydney City

6) Chatswood

About a 20-minute train ride from the city is Chatswood, a relatively young suburb that has exploded over the last decade into a hub of Sydney’s most authentic Asian tastes and a selection of shopping destinations that rivals the city.

Don’t mistake this for Chinatown – Chatswood is where Sydney’s wealthiest Asian families will often frequent. This suburb comes with two huge shopping centres, one that specially caters to the upmarket crowd fuelling their appetite for designer goods, and the other stocking popular international brands for a younger crowd.

For us locals who have gotten past the excitement of owning Sydney’s most beautiful modern shopping destination, it’s the food we can’t stop obsessing over. No joke: Chatswood has five different food courts in its concentrated shopping area, two of which were recently opened and designed with the look of Southeast Asia’s local street vendors in mind.

A personal favourite is the Hello Kitty cafe – it’s the standard American diner selling delicious sweet potato fries, juicy burgers and a healthy side of cuteness.

Top 10 Coolest Neighbourhoods in Sydney | Chatswood, Hello Kitty Cafe
image by Leah Davies via flickr

7) Darling Harbour

The iconic Darling Harbour is a long-time favourite destination for visiting tourists, and for one crucial reason: fireworks are held over the waters of the harbour, every single week from the months of May to October.

If you’re planning to drop by around December, Sydney’s New Year’s Eve fireworks simply can’t be missed. The entire harbour lights up in a spectacular display of lights, with half the city crowded around the shore to capture one of the world’s most magnificent firework shows.

For the non-fireworks days when visitors aren’t wrestling one another for the best photo spot, the food strips on both sides of the Harbour offer fantastic seafood menus that pair off with the neighbouring view. Make sure you book a window seat indoors – on some days, the seagulls can get slightly vicious here.

Top 10 Coolest Neighbourhoods in Sydney | Darling Harbour
image by Roanish via flickr

8) The Rocks

The Rocks mark the birthplace of modern Sydney with an intricate history that took it from being the shady suburb where convicts first settled to the hub of Sydney’s upmarket creative crowd. With such a vibrant local history, it goes without saying that this revitalised neighbourhood has its fair share of secrets, spun out of spine-tingling urban legends and some of Sydney’s shadiest historical events.

For those who aren’t impressed yet, I dare you to take a walking tour. The Rocks runs daily tours hosted by local historians who have studied every stone and etching made into the old colonial structures dominating this revitalised suburb. There is history in the things we take completely for granted and it’s fascinating how much you will learn.

If you’re after something more daring, brace yourself for the ghost tours that run every evening, taking you through the torch and lantern-lit laneways once home to street gangs, dank seedy bars and a rampant outbreak of the plague.

Top 10 Coolest Neighbourhoods in Sydney | The Rocks
image by Gil Baillache via flickr

9) Chippendale

Chippendale is where the cool Sydney uni students love to play after class, a suburb that maintains a vibrant edge as one of Sydney’s most rapidly gentrifying neighbourhoods.

The recent redevelopment of Central Park makes dropping by Chippendale an inner city trip you won’t want to miss. Once an old brewery that stayed closed for 150 years sprawled in a suburb renowned for housing hungry convicts, a team of architects decided to give it an identity that could capture an experience of living in harmony with the natural world.  

Channelling the infamy of New York’s Central Park, Sydney’s version is now a lush parkland, neighbouring one of our most infamous residential buildings. Known as One Central Park, this apartment building actually has 250 species of Australian flora planted to form a musical composition on the facade of the building. Vertical hanging gardens also stretch like tapestries across the outer walls, along with a huge heliostat operating a series of mirrors that reflects daylight across into the communal areas of the building. Although this award-winning structure is far too expensive for most of us to afford living in, it’s a magnificent sight to see.

Around the building, the nearby shopping strips have also taken on a new look over the years. A standout is Spice Alley, a series of authentic Asian food stalls hidden in the redesigned laneways curving around Central Park that bring an urban twist to the age-old cultural concept.

Top 10 Coolest Neighbourhoods in Sydney | Chippendale - One Central Parkl
image by Rob Deutscher via flickr

10) Potts Point

The affluent neighbourhood of Potts Point caters to a sophisticated crowd as the last remnant of Sydney’s Man Men meets Old Hollywood vibe in a time where the entire city is urbanising and remodelling to fit the demands of a contemporary urban crowd. Potts Point says to hell with it. With streets lined in trees and aged art deco buildings, the suburb offers a taste of some of Sydney’s most beautiful late-night haunts.

A favourite place of mine to drop by every time I’m in the neighbourhood is Eau de Vie, an award-winning New York-esque bar that stands as a shining reflection of Potts Point’s salute to the old world.

Top 10 Coolest Neighbourhoods in Sydney | Potts Point
image by Angus Fraser via flickr

Of course, this list is incomplete – there are so many more vibrant neighbourhoods nestled in some part of our wonderful city just waiting to catch visitors off their guard. Ask a local for their take on where the coolest suburbs are and you’ll almost always get a different answer.

For us, we call it home. But for travellers? Behind the veneer of our iconic Opera House and Harbour Bridge lies a world of blended cultures just waiting for the uninitiated to stumble upon and discover!

This is a guest post by Amy Cai.

Amy profile Amy is a journalism and law student hailing from the gorgeous city of Sydney. When she’s not buried behind her textbooks or filling her Pinterest board with armchair travels, she’s off exploring different worlds and taking amateur pictures along the way.