If there’s one thing we love, it’s a good time. We cut our teeth exploring wineries in South Australia and working at cocktail bars in Adelaide, before heading out into the world to explore dive bars in East London and whisky distilleries in the Scottish Highlands. Needless to say, we think we’re pretty qualified when it comes to recommending a good drink. Now that we’re settled in Sydney, here are our top five Sydney bars we’ve been to time and time again for a drink.
Caterpillar Club
The newest venture from much-loved hospo group Swillhouse, The Caterpillar Club opened to much hype at the end of 2023. Boasting one of the largest record collections in the Southern Hemisphere and one of the latest last calls in Sydney (3am weekdays, 4am weekends), this underground bar has filled a vacant space left in the scene since the close of Frankie’s Pizza.
With cosy booths, a colourful dance floor and a funky cocktail list, whether you’re heading for an after-work drink or a Saturday night boogie, Caterpillar Club ticks all the boxes. Be warned though this place is never without a line – but it does move quickly.
Old Mate’s Place
Hidden up the stairs (or the dodgy elevator) of an unassuming office building on Clarence St, Old Mate’s Place is a wood-panelled saloon spread over two levels. When it’s cold and rainy cosy up by the candlelight in the downstairs bar, and when it’s sunny and warm enjoy the rooftop space with a stunning view of the Sydney City.
My go-to drink here is Pandan Airways, which just came in at number 26 in the Drink of the Year awards. I wish I could tell you exactly what it tastes like, but every time I’ve been here it’s been a bit of a raucous time and I can’t quite remember. I want to say it’s fruity but light – you’ll have to head in and try one yourself.
Baxter Inn
This speakeasy is a Sydney staple, serving whisky and pretzels to thirsty patrons since 2011. Back when we were at uni and used to visit Sydney for this blog, we used to come to Baxter Inn after our events, so we’re both longtime fans.
One of the world’s best whisky bars, boasting over 800 whiskies across the back bar and in a rustic cave, you can try everything from house-pour staples to some of the most rare and expensive drams in the world. The vibes here are also immaculate – it’s just as perfect for an intimate date as it is for meeting new people and sharing whisky-embellished stories and bants.
The Lobo
A comforting favourite, whenever I need a cosy spot to sip a strong drink The Lobo is always front of mind. Focusing on rum, you can explore the back bar through one of their tasting flights or a carefully crafted cocktail. The dark, wooden interior is regularly lit by a burst of flame from behind the bar – is there a better garnish to a dark rum than a charred cinnamon stick?
Maybe Sammy
Consistently ranked amongst the world’s best bars (#1 in top 500 bars!), Maybe Sammy leads the bar scene with innovative cocktails served theatrically. The team here craft a new menu every season to a theme, with the latest drop being The Grand Maybe Sammy Cocktail Menu (with inspiration taken from The Grand Budapest Hotel). The immaculately-dressed staff serve each drink with a flourish, accompanied by bubbles, coordinated dances and interactive props.
They only take walk-ins here and be prepared for a line, but it tends to move quickly, even on weekends.
Images sourced from: Swillhouse, Old Mate’s Place, The Lobo, Maybe Sammy
