When all you need is a speakeasy night of tippling, look no further than Sydney’s Inner West.

Sydney can be so overwhelming with choices when it comes to bars. For this reason, we recommend a night out in the Inner West instead. You will be surprised what you find. From contiki-themed watering holes to thriving live entertainment, here are Sydney’s quirkiest Inner West bars.

Titus Jones

Titus Jones puts the “small” into small bar. This hole in the wall sits around 30-40 people max in a quaint, dimly-lit interior. The menu is limited and seasonal, but packs in as much as it can handle, including bar bites like tacos. But fret not, you wont feel crammed, but simply part of the furniture. It’s the perfect spot for intimate date nights or one-on-ones with friends.

Gasoline Pony

Add some ad-lib music to your evening at Gasoline Pony. Their live entertainment style is simple: any busker can book in to use the stage with their fees coming straight from the crowd. Did you love that band? Throw them a $20 in the tip jar at the end of the bar. They are strong on sourcing locally-made products, including a smartly designed bar bites section.

Lazy Bones

Serious music fanatics must not pass up a night at Lazy Bones, especially nearer the weekend. Nearly every night is covered, showcasing all sorts of eclectic bands; from ska orchestras to bluesy jazz duos. Matching your entertainment is an erratically stocked bar that is versatile on the cocktail front. Be sure to check out the delicatessen in the back for a bite to eat.

Jacoby’s Tiki Bar

At Jacoby’s Tiki Bar, you’ll feel like a pirate as you mingle with your friends in paradise. This oasis-themed venue serves up a quaint selection of crafty cocktails that are sure to wow all your senses. Think shared bowls of alcoholic punch in the shape of a sea shell, matched with pizzas from Manoosh Pizzeria next door. To be honest, you don’t come here and not order a cocktail.

The Imperial

The Imperial in Erskineville specialises in flamboyancy and spice, not only in their bar menu but even in their entertainment. You know it’s going to be a little different when the bathroom sign is a mixed gender symbol with the phrase “Whatever, just wash your hands.” By day, this place becomes a cruisy lunch venue upstairs, and by night it gets a little wild with all sorts of shenanigans.

Where’s Nick?

Where’s Nick? calls itself a small wine bar, but it’s quite sizeable considering the surrounding competition. The dimly lit interior is makes for a perfect intimate evening, with a secluded room out the back ready for bookings. Their menu focuses highly on wine, from quality to quirky, while serving up local beers and essential spirits. They even do special wine tasting events, so keep an eye out!

Tandem Bar

When you’ve had one of those days where your boss is being a pain or your coworkers are missing brain cells, Tandem Bar is where you want to end up. But Tandem Bar is more than just a sanctuary from life’s problems. It’s also a trendsetter. They serve aquavit as a menu staple, which is a Scandinavian spirit similar to gin. Break into the aquavit world with a four-shot tasting flight for only $30 at Tandem Bar.