“Oh, you hate your job? Why didn’t you say so? There’s a support group for that. It’s called EVERYBODY, and they meet at the bar.”
– Drew Carey
There are more than 7,000 languages in the world, and Drew Crey still chose to speak the fact. And Sydneysiders especially can relate to this… After a week of ‘quick calls’, answering emails that should never exist and pretending your CEO is fun, the only therapy that actually works is joining your mates for drinks. Lucky for you, Sydney is packed with spots that make catching up feel like a mini adventure—without the hiking boots or tents. From floating restaurants to speakeasies, here’s where to drink in Sydney with your friends…
Showboat Dinner Cruise
Sure sure, drinking at a famous pub or restaurant is cool! But mate, have you ever had a drink at a floating restaurant? If not, you’re missing out! Dining and drinking on the Showboat dinner cruise with a delectable 3-course meal, unlimited drinks and Sydney’s longest running cabaret show being performed exclusively for you? What more can you ask from a night out with mates!
And you thought that was the end? Nah nah! You cruise past architectural marvels that are Opera House and Harbour Bridge—with drinks in hand, some mates beside and memories made on the go! And if you’re cruising with a group, then you get the benefit of group deals and all-inclusive drinks packages.
Fortune of War
I’ve known seniors in my office flexing their work experience, but mate, how can a bar in Sydney do the same? That’s Fortune of War for you! FoW is the oldest pun in Sydney that has been hanging around since 1828 — and it flexes its credibility without those experience certificates. It’s a pub with character, complete with wooden beams, low ceilings and that unmistakable smell of history. And who knows, maybe your great grandfather might have had a beer here too. You could either dine and drink indoors or opt for al fresco dining! So, grab a schooner, clink your mugs and drink the day!
The Glenmore
If I had a dollar for every time I came across an antique pub in The Rocks, I would be a bloody millionaire by now! The Glenmore (pouring beers since 1921) is yet another oldie that still rules The Rocks… and when I say ‘rules’, I mean it literally and figuratively, because it is also a rooftop bar that overlooks Sydney—yes, you get great views of the Opera House and Harbour Bridge!
Down a jug of beer, crack the same inside jokes with your mates for the hundredth time, and enjoy that panoramic harbour backdrop—and boom, you’ve got yourself the definition of “Sydney vibes”. And, if you leave without at least one blurry selfie with the Opera House in the background, did you even go?
The Opera Bar
A ‘best bar in Sydney’ list is zilch without the Opera Bar… It’s one of those places where “just one drink” is a straight-up lie. You start with a beer, the sun sets, someone orders a round of cocktails “for the vibe”, and before you know it, you’re splitting a pizza at 10pm and convincing yourself this counts as dinner. The people-watching alone is worth the trip—you’ve got first dates trying way too hard, tourists losing their minds over the gorgeous views and office groups venting. At Opera Bar, life just feels a little bigger, a little better, and a lot more expensive if you don’t keep track of the rounds. But mate, when the Harbour looks this good, who’s counting?
The Caterpillar Club
The Caterpillar Club, an underground late night music bar, isn’t your “order a beer for fun” type of place. Nah, this one’s got a mystery. It’s the kind of bar where you half-expect to be asked for a password at the door (and it’s not “open sesame”). The inside feels like you’ve stepped into another world—dim orange lighting, luxe booths, bartenders who look like they’ve just come back from an art gallery in Milan. And they also claim the title for one of the world’s largest private record collections.
Drinks here aren’t just drinks; they’re borderline science experiments. One cocktail might arrive smoking like a chimney, another looking like it belongs in a jewellery case. And you’re sitting there with your mates, just wowed by the moment!
Baxter Inn
Finding The Baxter Inn is half the fun. You duck down an alley, past a door that looks like it hasn’t been opened since the 80s, down a staircase, and suddenly you’re in whisky heaven. Floor-to-ceiling shelves stacked with bottles, bartenders who somehow know the difference between 100 kinds of Scotch without blinking, and lighting so low you could probably get away with singing karaoke and no one would notice.
This is where you and your mates pretend to be sophisticated adults for an evening—nodding thoughtfully at a glass of whisky like you’re in Mad Men. Of course, the illusion usually breaks by the third round, when someone asks “why can’t the government print more money?” Sometimes, the best things in life find you, and sometimes you find the best things yourself—you find the Baxter Inn.
At the end of the day, Sydney’s drinking culture has something for every mood—whether it’s floating past the Opera House on the Showboat, downing beers in a pub older than your granddad, or hunting down whisky in a hidden basement. The drinks are good, the views are better, but it’s the laughs with your mates that make it legendary. So pick a spot, grab a glass, and let Sydney do the rest!
Author Bio – Amanda Clark
A Sydney-based travel writer who loves chasing experiences that defy expectations – especially when great food and entertainment are part of the mix. From unforgettable hits to unexpected flops, I share real stories to keep the adventure honest and fun for everyone!
