Okay, I Was Wrong: Sydney Is Cool

I’m in Sydney’s Ovolo Hotel in Woolloomooloo writing this. I had booked a last-minute trip to check out this year’s Vivid festival, and now, sitting in the charming hotel lobby, I’m getting a tad sentimental about this divisive city.

The first time I went to Sydney I hated it.

It was 2014, and I had managed to weasel my way into an internship with one of the country’s biggest news broadcasters — by literally just calling and asking for one. I didn’t expect them to say yes, so when they said can you come next month, I responded with: “Sure.” Even though the office was in Sydney, and I was in Melbourne.

Basically all the money I had went towards the flight to Sydney, so to save cash, I stayed in a dodgy hostel in the Cross, sharing bunks with 11 other people, speaking in a fake English accent to the staff all the while because this was a ‘traveller’s only’ hostel — which meant you needed to show your non-Australian passport when checking in. Lucky for me I had conveniently “lost” my “British” passport in “Thailand” a week previous.

The internship was fine, albeit underwhelming. Much like all of Sydney. A least it was to me, back then. But the cool thing about being alive is, sometimes you can change your mind on stuff — it’s totally fine! 

Fast forward to present day, and I’ve lost count of the number of times I’ve been to Sydney. That’s just the reality of working in media in this country — most of the jobs are in Sydney, and the ones that aren’t, still involve a semi-frequent pilgrimage to Sydney — it is, for better or worse — the centre of our great nation.

Each time I go to Sydney, I like it more. Hell, I might even be inclined to say I love Sydney — a strange kind of acquired love, like a disgruntled dad slowly learning he can’t live without the house pet he claimed to never have wanted.

Let’s dissect.

The pretentiousness

Sydney has always been the flashy sibling, hogging the limelight while Melbourne quietly cultivated its cool factor. I always felt Melbourne was ‘real’ while Sydney was populated entirely by posers. But I was young and dumb. Growing up is realising that Melbourne is actually full of a more insidious type of poser — go to any house party in Brunswick and you’ll be surrounded by trust fund nepo babies dressed in working-class cosplay. At least the posers in Sydney aren’t lying to themselves or anyone else, so in a way, even though Sydney comes off as more pretentious, they’re kind of more real for that.

She’s stunning

I know it’s a cliche to mention how beautiful Sydney is, but cliches are cliches for a reason my friend. Look out at the Harbour, and the Opera House, and I dare you to tell me you don’t feel anything — it’s impossible. Add to that its sparkling actual beaches (sorry St Kilda I love you but I would never swim in you), lush parks, and a Harbour that seems to stretch into eternity, Sydney effortlessly combines urban sophistication with natural splendour.

The trains

I am a simple man. I see double-decker train, I think: “This is neat, wish Melbourne had this”. Also touching on with your credit card and phone is such a nice quality of life improvement over the disgusting Myki system.

The food

Melbourne has always prided itself as the food capital of Australia, with its laneways packed with hidden gems and actually decent coffee culture. But Sydney is going through somewhat of a food renaissance.  

Sydney’s coastal location blesses it with a cornucopia of fresh and diverse aquatic delights. From succulent Sydney rock oysters to plump prawns, the seafood offerings in this city are just not a thing in Melbourne. It all tastes even better when you’re at one of the city’s waterfront restaurants, with a stunning view of the Harbour as your backdrop. 

It’s not just seafood though. Sydney Morning Herald recently claimed Sydney leaves Mebourne in the dust when it comes to top-notch restaurants — I wouldn’t go that far, but I will admit there are charms to Sydney’s restaurant scene that come close to the undisputed cool of Melbourne. 

Plus, one of the best-plant based restaurants in the country is located in Sydney, in the form of Wolloomooloo’s Alibi — an ‘indoor-alfresco’ dining concept serving up innovative Mediterranean veggie fare with real flair and soul. Eating at Alibi is genuinely a transcendent experience, and I say that as someone who very much enjoys meat. 

The unique combination of rattan seating, patterned tiles, and glass pavilion surrounded by lush tropical greenery provide the perfect backdrop for Shannon Martinez (the mind behind Melbourne’s much loved Smith & Daughters) and renowned mixologist Andre Gualdi to showcase their stuff in one of Sydney’s true highlight dining experiences.

The weather

OK I know everyone says this, but sunny days are really nice. And Sydney gets them in winter too. Wild to me.


Vivid is essentially Sydney’s unofficial winter festival, and the latest iteration was one of the best yet. The festival has grown into so much more than a mere series of lights at Circular Quay, it’s now a truly unmissable event you should experience at least once in your life.

The hills

Everything in Sydney is just a 10-minute uphill walk away. I have no science to back this up, it’s just my personal experience, which I value over science. Oh, friend wants to meet at a bar? That’s a 10-minute trek. Oh cool house party? 10 minute journey involving stairs(??) at some point. The city is an unorganised messy blob of hills designed to get you lost and break your spirit — and I know this sounds like a bad thing but it’s kind of fun to get lost, I’ve found some of my favourite bars this way (check out The Long Goodbye, trust me). And hey, a little extra cardio never killed anyone. So the hills are a good thing, actually.

The Ovolo

I know I’ve mentioned this place at the start of this story — but I’ve also mentioned staying in a 12-person dorm. I’ve been lucky enough to travel a lot in my 20s, most of that was done with a ragged backpack and a sleeping bag, at the cheapest hostel possible. I feel like it’s important to have that phase in life, but now that I’m old (30), I like sleeping in places that are nice — really nice — places that are stunning, actually, places like Wooloomooloo’s Ovolo.

I’m rarely a hotel simp. In fact, this is my first time publicly hotel simping, but I’ve never stayed in a hotel like it — the kind of hotel you almost don’t want to leave because it’s so damn nice. Bridging modern luxury with the unique heritage that comes from the rich history of its wharfside home, it’s complete with all the stuff you’d expect from a modern hotel (gym, pool, etc), plus a breakfast buffet that is literally to die for, Willy Wonka glass elevators, lolly bar upon entrance, delicious welcome snacks, and a free(!) minibar. 

Plus the location can’t be beat if you’re coming from out of town, as it’s a stone’s throw from the Sydney Harbour and Opera House. It’s the only place I stay whenever I’m in town. 

The writer flew to Sydney as a guest of Booking.com.