Have dinner and wine upstairs, then head downstairs to party.

Cantina Ok! is a 20-seat cocktail bar specialising in rare spirits from Mexico. It’s in a tiny garage at the end of a delivery laneway, manned by three jovial and variously bearded barmen in white aprons.

Reign is a posh, light-filled 140-seater with brass detailing, hues of pink blush and gold, plus marble on nearly every surface. Run by an all-women bar team, drinks are garnished with decorations such as origami crowns, paper planes and music sheets, and there’s more than 180 whiskies and 200 wines from around the globe.

Whisky, cognac and "shit tinnies" are your reward for finding this rowdy bar. Just look for the three skulls.

Esquire in the Queen Victoria Building is a moody New York style supper club. It’s a beautiful space for long business lunches but also – and importantly – late-night snacking and drinking.

The Push is an intimate bar beneath the Russell Hotel with a focus on cocktails and down-to-earth pub-food such as burgers and steaks.

To get to Bowery Lane, you step inside a set of office-like sliding glass doors. But rather than walking straight into another of Sydney’s sky-high office buildings, a sharp left will take you into what feels like a Manhattan loft.

A classic CBD Friday afternoon atmosphere but with a more interesting beer list, and a mix of American and Italian sides such as lamb ribs with garlic and lemon; or smoky fried chicken wings.

The Ramblin’ Rascal crew’s second venture is named after the dive bar in the 1989 Patrick Swayze movie Road House.

Below pavement level on King Street in the CBD there’s a den of New Orleans-inspired drinks, food and jazz. Pete Fischer is behind this small bar and it is the culmination of all his extensive bar experience to date, delivered with moody vibes and clever simplicity.

Grain is decked out with an abundance of timber, a gas fireplace and cosy amber lighting. Settle into the matching Swedish neo-retro furniture and you can peruse a whisky list with more than 240 entries sourced from Scotland, Japan and Australia.

Found on the third floor of the Republic Hotel, the bar is accessed from Tank Stream Way and then via a substantial flight of stairs. The climb reveals an open-air space that's admittedly more roofless than rooftop, but the air is cool and Pitt Street's skyscrapers wink down from above.

The drinks list at Burrow Bar switches up every couple of weeks. The barrel-aged cocktails sell out fast, and the shrubs (tangy, refreshing drinks made from vinegar-based fruit syrups) are popular too. The team also makes its own infused liqueurs and rums.

Influenced by the soldiers and machines of the Second World War, Kittyhawk brings rye and rum cocktails to the business end of town. The bar’s concept imagines liberation day in Paris.

Bar Odessa, the plush basement bar at David Tsireka’s Greek restaurant 1821, was inspired by the history of the Greek Revolution. The bar is at the bottom of a narrow, dimly lit staircase. Once inside, Bar Odessa promises luxury fit for a Tsar with an extravagant suite of caviar alongside other Black Sea indulgences: pates, oysters and smoked fish.

Everything from Three Bottle Man is served in threes – three varieties of gin, three beers, three reds, three whites and so on. They change each week but they’ll always be Australian, most likely boutique producers too.

The waterside location may be quintessentially Sydney, but the exposed copper piping and enviable list of craft beers is less aligned to the usual King Street brief. The beer, too, bucks the trend of super hoppy, heavy IPAs.

For seven years this spot was Shirt Bar but in 2018 it was reimagined as The Bandit’s Roost, a cafe and bar with a deli-style menu, an extensive whisky list and well-made coffee.

The bar, which opened in 2004 with an unassuming door and a notoriously misleading “Psychic” neon sign, was a pioneer of the city’s reinvented cocktail scene. It’s since come to be regarded as one of the best cocktail bars in the world, thanks to its well crafted but evolving cocktail list and switched-on staff.

Bar Topa is a pocket-sized contemporary tapas bar. It only accommodates 40 standing diners and a few on stools that are scattered about. It’s a place to pop into for a couple snacks before heading on to the next venue.

The 98-capacity venue is filled with brown-leather booths in front of bookcases, and foliage peeping from every nook and cranny. To access the drawcard rooftop bar you’ll need to climb another set of stairs (this space closes at 10pm). There’s more greenery and punters have 360-degree views of the city’s skyscrapers.

At 1950s Vegas-inspired cocktail bar Maybe Sammy, there’s a rotating tasting menu of $10 classic cocktails served in mini form. The space has plenty of green, pastels and gold, and bartenders kitted out in pale-pink dinner jackets. Plus, there's a $2 oyster deal on Sunday afternoons.