The best bars in Sydney's CBD right now

The team behind Sydney’s tiniest and coolest Margarita boozer, Cantina OK, are behind subterranean tequila bar, Centro 86. Meaning centre in Spanish, Centro 86 is hidden in a CBD basement on Pitt Street (entry is via Hoskings Place) in the centre of Sydney’s high-rolling and drinking action. And while tequila and Margaritas are the specialty at Centro 86 – there are 100 tequilas on offer, including some ‘world's rarest’, plus five signature Margs – don’t expect just a bigger version of Cantina OK. Instead, creative director Jeremy Blackmore says you’ll stumble into “an old fancy Mexican cantina on shrooms.” Add on cracking service and Tio's famous popcorn, and you'll be in for a good time indeed.

If, god forbid, anyone ever flipped on the grown-up lights at the Ramblin’ Rascal, what might it look like? A barely renovated former comedy club in the basement of a nondescript city office block full of dentists, orthodontists and maxillofacial surgeons. The booths are vinyl and the carpet is – well, the less said about the carpet the better. Eyes front, people. But show us another bar team in the state that can so readily be recognised by their skull logos alone. The rascals who make up the core team at the Rascal are so clearly delineated in look, roles and manner they might as well have their own trading cards.

Located at the top of Shell House, Sky Bar is an Art Deco dream in earthy hues – a palette of burnt umbers, rich terracottas and creamy tones. The design throughout these upper levels of Shell House is a luxurious ode to the building’s unmistakable clock tower – a glazed stone monolith watching over the Sky Bar’s alfresco terrace. If you're looking to impress or keen for a special late-night tipple, Sky Bar is a dependable – and good-looking – choice.

Firstly, come to The Caterpillar Club. With DJs and live music every night, '90s-inspired cocktails, and a banging cheeseburger, it's the city's hottest bar for good reason. But because half of Sydney also wants to come, you need to time your visit right. We suggest heading down early – either at 4 or 5pm – to snag a coveted seat, or after midnight for a late-night drink (The Caterpillar Club stays open until 3am). But if it's 10pm? Forget about it. The Caterpillar's tail is too long.

More bartenders should sport double-breasted dinner jackets. More cocktail bars should play jazz hits and lounge covers at conversation-enhancing volume. And more hosts should welcome guests as eagerly as owner Stefano Catino does at Maybe Sammy. It’s a polished affair bathed in Golden Age glamour. Creative director Andrea Gualdi has assembled one of Sydney’s most pedigreed squads of shakers and stirrers, and their commitment to quality is apparent in almost every glass.

Stop me if you’ve heard this one: Barbarella, the Jetsons and Austin Powers walk into a bar… The vibe of the top-to-bottom refurbishment of Sydney Tower’s top floor, now home to the loftiest cocktail lounge in the city, is not so much a nod to the ‘60s as it is a full-throated power ballad to the kitschest, campest, most swinging design trends of the age. Sitting 83 storeys above street level, it's got killer views of the city and beyond, and in addition to a delicious cocktail list, it's also open until 2am.

When Shady Pines Saloon opened in 2010, we thought we’d met the bar we wanted to spend the rest of our lives in. Then we met its little brother, the Baxter Inn, and there was a serious challenger for our eternal affections. Of course, we weren’t the only ones enamoured with the backlit wall of whisky, accessible only by scrolling library ladders or by having your well-coiffed bartender climb along the counters like some sort of arborial gentleman. The lines of admirers stretched from outside the tatty door in an old loading dock in the city and almost back out onto Clarence Street. This is the kind of whisky collection that would make a strong man weak at the knees.

There is no bar in Sydney embracing the mad craft of cocktail experimentation as whole heartedly as the team at PS40, nor any having as much fun doing it. They almost seem to take it as a personal challenge, which is why they’ll take your milk punch and raise it with a King’s Cup of leftover spirits infused with honeycomb, poppy seeds, caraway, grapefruit, mandarin and whey. 

At the end of a service alley, a step back from the CBD bustle, gold light spills out onto the asphalt. There’s a scent of lime in the air, the sound of Boston shakers, and somewhere behind it, just a hint of danger. This is Cantina OK, the standing-room-only bar that since February of 2019 has plied Sydney with good, clean, sort-of illicit fun fuelled by mezcal and backed up by one of the sharpest bar teams in the city. Pick a day – any day – and the Cantina will be rocking it, two or three tenders ably servicing the 20 or so drinkers who cram in at any one time from when the roller door opens till close at 2am.

Kittyhawk is exactly the sort of place you want to feel liberated from your inbox at the end of the day. The knowledge that gracious service, ace drinks and excellent food are waiting for you makes leaving the office on time that much sweeter.

In the basement of a heritage warehouse in Sydney’s CBD you’ll find a Sicilian-inspired cocktail bar named for the ill-fated wife of Michael Corleone in Francis Ford Coppola's 1972 mobster masterpiece, The Godfather. But don’t let that put you off. For those of us who have been lying about having seen The Godfather their whole lives, good news. Every page of the drinks menu will run you through the storyline (spoilers lie within, but it’s literally been 50 years) so you can impress your date with cinematic knowledge while sipping on a Letter Never Sent, a standout concoction of wheat vodka, honey liquor, pineapple, clove, housemade almond syrup and fresh nutmeg, shaken and served over ice.

Created by the team behind multi-award-winning cocktail bar Maybe Sammy, this lofty lounge isn’t just resting on the laurels of its penthouse perch, 22 storeys up atop the A by Adina hotel tower. George Livissianis’ interiors are a glossy timewarp of tiger-striped carpets, dusky-veined black marble, leather upholstery and brushed brass accents that mirror both the amber sunsets in the afternoon and the golden illuminations that light up the double-height ceilings after dark. It’s Vegas. It’s Mafia-chic. It’s the Rat Pack and Mad Men and Frank Sinatra crooning to Monroe and Kennedy. 

Things are thoroughly cheeky at the Ramblin’ Rascal Tavern's second venture, down in a booze-stocked, retro-panelled bunker straight from Boogie Nights, with a soundtrack to match. The crew, too, look every bit the part – rocking bowling shirts, booty shorts, tennis socks and slick quiffs, all too eager to hand you a VHS case with a risqué cover that turns out to be the drinks menu. Elsewhere you might find yourself flipping through pages of punny names, garish descriptions and outlandish illustrations before landing on something you’d consider knocking back, but not here.

With excellent cocktails, old-world charm, and bottles of wine starting at $50, there's more than one reason to come on down and make friends with Charles. And we really mean excellent cocktails. This sexy European-inspired bar features innovative tipples including a bright and tropical Mango and Yuzu Martini served with a white chocolate stuffed olive, a punch made from Loulou’s golden croissants swirled with rum, passionfruit, vanilla, garnished with meringue and passionfruit gel, and a strawberry and basil twist on an Americano featuring forgotten fruit and house-made basil cordial

One hundred and two steps. Rooftop bars are not for the faint of quad. But all that thigh-burning just primes you for the reveal: swing open the door at the top and there you are, in a lushly planted oasis in the Sydney skyline. A smiling bartender hands you a VB throwdown while you flip through the menu. A bowtie is slung around their neck unknotted, Rat Pack-style. It might only be a quarter past six down on street level, but up here, it’s always time to take it easy. 

You could definitely jam a dozen or so more bodies in the 60-seat space, but this is a civilised place, a table-service-only zone with very limited standing room. Save for the glass frontage, there are no windows inside, which lets the moody, monochromatic forest-green colour scheme cast a very seductive spell. When you settle into a sturdy chair or a bouncy stretched leather banquette, a member of the very attentive, waistcoated waitstaff will place a dainty ramekin of devilishly addictive spiced nuts on your little table and ask you what kind of water you’d like.

This underground rum bar below Clarence Street is named after Cuban sugar baron Julio Lobo. A cluttered but cohesive mix of flamingo tiles, rattan chairs, banana palms and crumbling patina surfaces provide weathered Cuban charm. But the real visual focus is the bartenders. They create with precision. And fire, if you order the Old Grogram. Slip into the Chesterfield booth seating and prepare for a fabulous tiki mini-break for your mouth (the kitsch cocktail illustrations on the menu will help you decide on a destination)

The brains behind legendary Sydney bar Old Mate’s Place and Newtown’s speakeasy-style tropical cocktail boozer Huelo are at it again – this time with a Caribbean-inspired rum bar affectionately named Old Loves. Found in a dark and moody basement on Clarence Street, this hidden spot boasts a 320-strong rum list with a fair share of rare and exciting tipples. The team also has a sugar cane press, which allows them to juice sugar cane fresh to order, so guests can enjoy a variety of rums without tasting them neat or on the rocks. Now that’s neat.

The Duke of Clarence boasts all the trappings of a 19th Century tavern, right down to the potted red geraniums above the door. They can pull you a perfect pint of Guinness, but really, this is a bar in pub’s clothing: a slender, licensed slice of the city designed to transport you to a different time and place. The sincerity elevates it above a themed bar – everything looks, feels and smells expensive, from the floorboards imported from the UK to the bubbled glass dividers, framed lithographs and the gin-scented handwash in the bathrooms.

A big part of the reason everyone’s trying to cram in here is the tiny drinks. For anyone who loves the social aspect of an afterwork bevvy but doesn’t jive on gallons of mid-week booze, may we present this teeny Martini, a 60ml three-sipper. And it’s brought its friends: the mini Negroni, the 100ml pour of a minerally, savoury viura from Rioja; and a smashable, citrusy sangria on tap that’s served with enough ice to withstand a heatwave. Short drinks mean you can go on a beverage safari any time and stroll, not roll, home. Brilliant. 

They’re not afraid to serve the Bitter Truth at Sydney’s hidden voodoo bar, and that’s because it’s an excellent cocktail, and not your friend telling you how badly you disgraced yourself the night before. A bracingly sour mix of lime juice, Averna and bitters is balanced by sloe gin, and it’ll soothe ruffled feathers and stop a shame spiral in its tracks. 

Now & Then has a pretty cool concept: the cocktail and wine bar celebrates the best cocktails, wine and beers from the past – as well as the ones we’re loving right now. In fact, there’s literally one menu called ‘now’ featuring tipples of the moment, as well as a separate menu called – you guessed it – ‘then’ with twists on retro classics.

‘Alley’ is a fair term here, given that headlights from cars leaving the garage opposite shine into the bar giving everything a slightly upmarket Blade Runner glow. The space used to be a conference room belonging to the Ultimo Hotel, but it’s far better as a sleek whisky bar in muted tones, where they have installed whisky lockers if you’re fancy enough to spring for a whole bottle that you’ll slowly drink on concurrent visits.