Review: Sydney bar tour reveals the city’s coolest drinking dens inner banner

Review: Sydney bar tour reveals the city’s coolest drinking dens

Quirky themed bars, cool cocktail lounges and speakeasy-style boltholes are breathing new life into the Sydney CBD after dark. This friendly and relaxed guided walking tour reveals some of the most interesting options.
Sydney bar tour
Sydney bar tour. Image: Ruby Boukabou
Sydney Bar Tour


On this intimate tour you’ll explore Sydney’s emerging small bar scene with a friendly local guide. Visit three unique CBD bars, sample delicious bar snacks and small plates, and learn some of the rich history of Sydney along the way. Duration: 3 hours (approx.)

Please note: Sydney Urban Adventures has recently discontinued this tour. You may like to visit the highlights listed yourself, or browse all our available Sydney walking tours here.

While the Sydney CBD is often considered too commercial, too corporate and too impersonal to bother with when heading for a night out (unless you happen to be knocking off work and looking for the closest option), things have thankfully changed.

The once exorbitant cost and complexity of liquor licenses was reduced a few years ago, encouraging enthusiastic and creative local entrepreneurs to bring after-hours-Sydney back to life with a swag of new intimate themed bars — many with innovative food options on offer.

Sydney bar tour
Sydney bar tour. Image: Ruby Boukabou

Sydney Urban Adventures, which operates under the Intrepid Travel group banner, is doing its bit to bring residents and visitors up to speed on the latest venues. The company’s popular Sydney bar tour promises visits to a number of hidden and tucked-away bars, and includes a couple of drinks, a selection of bar eats, and colourful tales of old Sydney town thrown in along the way. Being an often-overseas-based Sydneysider (just back in the country), I’m keen to join the tour to see what I can discover (or re-discover) in my home town.

There’s a drizzle of rain as I meet tour guide John at the glass dome opposite the York Street exit of Wynyard train station just before 6pm. He tells me it’s a small group tonight — an ex-advertising executive from the UK (in training to lead these tours), an American couple, and myself. This sounds fine to me. It will be nice and intimate. The maximum group size on this Sydney bar tour is 12 guests.

John leads us back down the escalators at Wynyard — the longest in Sydney — telling us that he was sad when Sydney Rail took out the historic wooden treads for safety reasons (commuters’ work boots and heels would often get caught in the gaps). As we get to the bottom he tells us that he was also relieved when instead of throwing away the treads, they were transformed into a piece of art. We look up and see the installation on the ceiling. I’ve never noticed it before! These tours are not just for tourists; locals will learn a lot too!

Sydney bar tour
Sydney bar tour: Wynyard railway station. Image: Ruby Boukabou

John is jovial, our trainee guide is lovely, and the older American couple are terrific, so we soon get into a comfortable roll of conversation and pull up pews at the first small bar, called (and situated in) York Lane. The split level bar feels a bit like you’re in someone’s converted garage. ‘Sydney we need to talk’ is painted in black on the white walls, and paraphernalia (including a bike on which the owner toured France) hangs on the wall as decoration. John explains that Sydney was intended by the British to be a ‘dry colony’. He describes the underground drinking scene that emerged as authorities launched Australia’s prohibition era, and how rum was the colony’s currency of choice. We sip an included wine (or beer) and take it all in, before continuing on down the lane.

Officially, the tour visits three bars and stops for 45 minutes in each. Back up on York Street, John also points out restaurants of note along the way, including what he says is one of the best pizzerias in the CBD. The chefs smile at us from the open kitchen. We head down some stairs and pouf! — we’re transported into what was once reputed to be a 1920s Chinese opium den! Uncle Ming’s is all about cocktails, Japanese whisky and Chinese dumplings. Red lanterns, Chinese art and portraits, and intimate seating areas are being appreciated by locals in-the-know as they sip various concoctions and chow down on delicious dumplings.

Sydney bar tour
Sydney bar tour: Stitch Bar. Image: Ruby Boukabou

We’re out in a flash (places to go, bars to see) and it almost feels like we could have had a group hallucination (did that just happen?). We soon descend to our next stop — Stitch Bar. Down some stairs, and hidden behind what appears to be a seamstress’ workspace, this cosy speakeasy bar with cute booths, cool lamps, old newspapers as wallpaper, and up-scale Americana-stye fare is a winner. I’ve been here once before and loved it. John orders some shared food plates and we buy a drink (there’s a great cocktail list).

We could all quite happily stay on here, but there are more places to discover and we head out into the night air. We pass several other bars, going into some for a look, and sometimes just peeking down an alley, up a staircase or past a shop facade. Every CBD nook and cranny suddenly looks enticing, and potentially like an entrance to a small bar! There’s a gin-themed bar, an absinthe bar, and a laneway leading to three bars — including one with a barber shop behind it (you can sneak backwards and forwards between the bar and the barber shop before a certain hour), and a 1920s-themed whisky bar that looks so amazing I’m tempted to abandon ship right here.

Sydney bar tour
The Baxter Inn. Image: Ruby Boukabou

Finally we arrive at Small Bar on Erskine Street and head upstairs to a table reserved for us. More hot snacks and a bottle of wine appear. It’s just after 9pm but the three hours have whizzed by. We share our thoughts on the tour with John, and all agree it’s been a very pleasant evening. All good things must come to an end and I take my leave to head for home. Then again, there is that whisky bar…

The writer travelled as a guest of Sydney Urban Adventures.

Additional images: Bigstock

About the writer

Ruby Boukabou is a travel, culture and food writer based between Europe and Australia. She has written for The Age, The Australian, Qantas, Issimo, The Diplomat, Paris Voice and Inside Film. She has also produced culture and travel stories for the ABC, SBS and Screen Australia. When Ruby’s not writing, she is probably tap dancing. She is a founding member of the Paris Tap Crew (which produces the monthly Paris Tap Jam) and a member of jazz/world music group Le Shuffle Project.


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