Don’t let the ambivalent name fool you, Maybe Sammy is definitely where you want to end up later tonight. Named after Rat Pack member Sammy Davis Jr, this Las Vegas-themed bar serves tipples that are far from the typical, with many presented alongside magic tricks and sensory performances. There are drink movers and shakers behind the bar, including a former Bartender of the Year. It’s no wonder Maybe Sammy is considered one of the best bars in the world (it’s ranked 22nd to be exact). 115 Harrington Street, The Rocks. maybesammy.com.

Many of the best bars in Sydney’s CBD are underground. Why is this? Is everyone seeking a furtive corner to nurse their drink in? Or is there something glamorous about descending down a set of steps and into another world, so separate from the hustle and bustle of the city? In the case of The Baxter Inn it’s definitely the latter. This dark wood-panelled bar, with a huge wall of backlit whiskey bottles screams nocturnal elegance. Lean into it and sit up at the counter with one of the best old fashioneds that you’ll ever drink. 152-156 Clarence Street, Sydney. thebaxterinn.com.

It’s all about the good vibes at this basement dive bar, where everything from the potent cocktails to the food menu – takeaway Mary’s burgers and fried chicken from around the corner – come served with a side of humour. Strike up a conversation with one of the overall-clad barmen if you don’t believe us. There’s a good chance that it’s one of the three owners, Charlie Lehmann, Dardan Shervashidze or Sebastian ‘Cosmo’ Soto, who all regularly take shifts mixing up one of their cognac and vermouth-laden specialties. 60 Park Street, Sydney. ramblinrascaltavern.com. .

One of the world’s best bars has opened in a heritage-listed basement on Barrack Street. Obviously cocktails, and sophisticated ones at that, form the bulk of the drinks menu. Alongside some of New York’s favourite drinks you’ll find some Aussie originals, including an avocado, lime and Pisco concoction. 9a Barrack St, Sydney. employeesonlysyd.com.

From the rattan chairs to the fringed foliage to the army of thick crystal glassware that each rum-laced cocktail is served in, visiting The Lobo Plantation is like taking a sabbatical to the Caribbean. Rum agnostics will have to settle for a glass of wine, however, as all the cocktails contain the sweet, sugary spirit. (Our favourite? The colonial sour tinged with earl grey infused malbec.) While you’re getting in the island mood, make sure to get a plate of flaky empanadas, too. 1/209 Clarence Street, Sydney. thelobo.com.au.

And now for something completely different. Fancy watering hole, Frankies ain’t. This underground pizza restaurant and live music venue is grungy and a little bit grimey but it’s also guaranteed to serve you an epic night whenever you go there. The pizza, sold by the slice, is always hot and the drinks generous and ice cold, though it’s really a case of choosing between beer, wine, the usual shelves of spirits or their fanciest tipple – also their best – a rum and fresh apple juice. If you’re up for an adventure, try to worm your way into their secret whiskey room. The doors open at nine, after which you’re on your own. 50 Hunter Street, Sydney. frankiespizzabytheslice.com .

Part of the fun of bar-hopping is getting to people watch, and the people-watching doesn’t get better than at Bridge Bon Appetit. That’s because you’re literally sitting atop decadent French restaurant Hubert on the mezzanine level, meaning you can nurse a glass of red – the bar boasts 550 different bottles of wine to choose from – while you peer down at the diners below. The food menu is a tight edit of oysters and caviar, but if your stomach starts to rumble just head downstairs and take a seat among the watched, rather than the watchers. 15 Bligh Street, Sydney. restauranthubert.com.

Named after its laneway location, this pint-sized cocktail bar in Circular Quay is known for its stellar cocktail list which gets a fresh shake-up every day. A team of expert bartenders create five tipples a night, which is scrawled out on butcher’s paper from lightest to heaviest. Since opening in 2012, the cocktail bar has made it on to World’s 50 Best Bars list four times and right now it’s ranked a not-so-shabby 75. Level 1/10-14 Bulletin Pl, Sydney. bulletinplace.com.

The cool kids behind inner-city dive bar, Ramblin’ Rascal Tavern, have opened a 70’s-inspired “porn-chic” cocktail lounge in the Sydney CBD. The interiors will take you back to the glory days of the 70s with its smooth, curved edges, timber pannelling and drab palette of mustard, maroon and brown. Despite the furry kissing booth and raunchy Playboy posters, don’t worry clothes are kept on, at least for now. Head bartender Oliver Churcher has created a list of ten cocktails, which see new twists on old favourites, while Mike Bennie from P&V Liquor Merchants has put together a wine list that includes everything from bold Burgundys to Fuddy Duddy Shiraz. 6 Bridge St, Sydney. doubledeucelounge.com.

It’s loud, brash and jam-packed with revelry, and although Prince of York appears to be another run-of-the-mill CBD swill house-cum-restaurant, what’s actually happening here in regards to service, wine and on the plate is really quite exciting. With multiple floors layered with mezzanine levels and all manner of nooks and crannies – the main bar, a restaurant/wine bar (Cellar) and a nightclub (Pamela’s) beneath – Prince of York is cleverly designed to make each space feel intimate, even though it’s licensed for more than 300. 18 York St, Sydney. princeofyork.com.au.

Who would have thought that one of the chicest live music venues in Sydney is the marble-lined basement of the Hilton hotel? But that’s exactly what Marble Bar is, a heritage-listed drinking spot dating back to 1893 that regularly plays host to soulful jazz singers and a sophisticated crowd looking for a night out to remember. With one of the best happy hours in the city, there’s never a dull moment at this bar. Level B1, 488 George Street, Sydney. marblebarsydney.com.au .

Jake Smyth and Kenny Graham of the famed burgers have revived the subterranean space once home to legendary live-music venue The Basement. A line-up of bands big on jazz, soul and R&B play to diners seated at spotlit tables and high-backed stools at the bar, where you can have the entire menu. You could do worse than start with the dirty martini, The Filth & the Fury. Rather than the classic olive brine, the ‘dirty’ comes in the form of bush tomato – infused in the Poor Tom’s gin and skewered with a tiny swatch of melted cheese as the garnish. Wines are largely local and French, with solid showings from Italy and Germany, a mix that neatly mirrors the European-leaning modern Australian menu. 29 Reiby Place, Circular Quay. marysunderground.com.

There are almost 900 different spirits behind the bar at Kittyhawk, a chic cocktail bar in the heart of Sydney’s financial district. 900! Just imagine, 900 different kinds of alcohol waiting to be whipped into whatever fanciful, old-school drink the bar staff at Kittyhawk can dream up. From the team behind The Lobo Plantation, the vibe here is less island paradise and more French liberation-era decadence. As in, the war is over, let’s have a good time. The cocktails include the Thunderbird (rum, aperativo, pineapple iced tea) and the deadly Celine, a combination of gin, dubonnet, peach shrub and absinthe. 16 Philip Lane, Sydney. thekittyhawk.com.au.

A former CBD-based garage has been transformed into Sydney’s latest drinking haunt. Cantina Ok! is the younger new sibling of much loved Surry Hills institution Tio’s Cervecería, a space so intimate that it’s largely standing room only, with a couple of bar stools thrown in for good measure. Settled into bustling Clarence Street, Cantina Ok! is an ode to Mexico and its rather lively late-night bars. The petite enclave is a vibrant den of pinks and pine, specialising in Mexican rare spirits, in particular, mezcal. Council Pl, Sydney. cantinaok.com.au.

Check out our list of 10 best bars in Sydney’s Surry Hills.