Getting caught up in city life and always heading to the same bars and restaurants we know is something we’re all guilty of. Being in the beautiful city of Sydney for a while now (and often sticking to my local neighbourhood of Paddington or Bondi for a night out) I decided it was time to explore and discover some new bars and restaurants a little less well known. Using the online publications Concrete Playground and Timeout I mapped out a bunch of bars to try which are highly rated and only known through word of mouth.

Finishing work in the CBD at 5pm, I couldn’t think of a better place to meet my friend and start the night than Establishment. With its uber chic interior and city worker vibe, this was the perfect place to kick things off. As a Merivale owned bar it was the June happy hour 5-7pm, so we got going with two Espresso Martinis half price! If I’m honest the bar staff were under pressure for the happy hour, so our Martinis didn’t have the best creme, but certainly quenched our thirst after a day in the office.

Next we had a short walk over to The Rook, which after asking a few people we found the entrance to – an elevator at the bottom of what looked like an apartment block. This hidden rooftop did not disappoint with a brilliant wine selection, old school music tunes playing and atmospheric lofty vibe. We guzzled a glass of Montepulciano red wine and were tempted by the delicious aromas of lobster and chips from the kitchen.

Going from rooftop to basement, we walked over to Baxters. With it’s entrance behind an alley and down an old fire escape, this underground speakeasy whiskey bar is super exclusive with a buzzing vibe. The walls behind the bar are stacked ceiling high with hundreds of whiskeys and it feels like a step back in time with the barman climbing the ladders to select your tipple. We couldn’t get enough of the freshly blended apple as a mixer for our whiskey – I won’t have my whiskey any other way now! Hopping next door, we had a quick drink in The Duke of Clarence. This typical British style pub was very warm and cosy and beautifully decorated like the drawing room of an English country home. We enjoyed our glass of wine in front of the warming fire with a bowl of complimentary smoked nuts.

Having completed a good round of the CBD bars, we caught a cab up to Paddington to devour yet another glass of vino at 10 William Street. This small wine bar in the heart of Paddo offers a range of delectable Italian tapas alongside an extensive wine list. A favourite for locals with its intimate yet bustling ambience, it feels like you could’ve stumbled off a street in Europe as you sit knee-to-knee with fellow diners.

Deciding it was time to get some food to soak up the concoctions of wine and cocktails we’d consumed, we visited Cheeky Burger! This late night joint sells simple burgers done well in a trendy American style setting. We halved a veggie mushroom burger and pulled pork burger and it was agreed that the veggie choice was a clear winner! To complete our evening we popped next door to The Paddo Inn to have one last drink. This pub is a local haunt and always busy with regulars no matter what night of the week.

Overall I was happy that we got to explore so many bars off the beaten track which I will be keen to visit again. My favourite find was The Rook with its top secret elevator entrance and offerings of lobster to enjoy alongside that perfect glass of wine. It’s also been a fantastic month for the numerous Merivale bars across Sydney, as they’ve been offering their 49% off drinks 5-7pm everyday throughout the month of June – Bottoms Up Sydney!