Time Out Sydney Bar Awards: Past winners

Earl's Juke Joint
Bartending is in many ways the study of party alchemy – mixing drinks to lift you up, cool you out and caress your soul if it’s in need of a little TLC. A well made Singapore Sling can send your tongue on a exotic getaway, even if the rest of you has to stay right here and pay the bills; a daiquiri has the power to convince your hips you’ve got the rhythm in you; and an Old Pal can be your best friend after a long day in the salt mines. And there’s nowhere we prefer to pull up a stool and bend the elbow than at the long, sturdy, timber bar at Earl’s Juke Joint.

Ramblin Rascal Tavern
If we told you there’s an underground bar in the CBD that is putting Cognac in everything you’d be forgiven for picturing a snooty Harvard-style lounge bar full of sharp-suited gents and elegant women. And it certainly is a well-heeled crowd at the Ramblin’ Rascal Tavern. But that’s probably due to it being beneath one of the most powerful magazine publishers in the city. Location, location, location. But straight-laced this bar is not.

Bulletin Place
Three years ago Bulletin Place gave the Sydney bar scene a haymaker it never saw coming. The little DIY attic above a café down near Circular Quay was not where anyone expected to find the city’s best fruit-driven, seasonal cocktail menu. We weren’t used to having a new set of drinks to discover each time we remounted those creaky timber stairs, and we sure as heck weren’t prepared for a raspberry cocktail that would melt our heart instead of making our skin crawl.

Papa Gede's
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 tiki bitters is balanced by sloe gin, and it’ll soothe ruffled feathers and stop a shame spiral in its tracks. Want something gutsier to fortify your spirit? Old Fashioneds and barrel-aged cocktails might be a dime a dozen in Sydney, but the fig and walnut version they serve at Papa Gede’s is the one we want to drink most. It’s rich, mysterious and pricks at your childhood nostalgia with a flavour reminiscent of squashed fly biscuits.

The Baxter Inn
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.

Rockpool Bar and Grill
So, we’ve been writing about this thoroughly realised bar since it opened back in 2009, which in bars years in Sydney, is a lifetime. The towering brackets of shining Riedel glasses, the house-made syrups and sodas, the astounding bar food menu thanks to Neil Perry’s neighbouring restaurant, professional staff operating the shakers – all of it adds up to a benchmark cocktail bar.

Barber Shop
Historically, gin has had a PR problem. Gin mill’s were places of ill-repute; gin itself was the source of Mother’s Ruin, and one Irish comedian described the juniper-flavoured spirit as mascara thinner for its supposed propensity to make girls cry. But gin wasn’t bad, it was just misunderstood, which is how it has gone from zero to hero of the Sydney bar scene in 2015. And the Barber Shop was one of its earliest cheerleaders.

The Cliff Dive
The tiki bar and nightclub that began filling its dancefloor since November 2013 took a bit of a hit just a few months later when Sydney’s new liquor licensing laws came into play. Once famous for their late-night parties, TCD had to start shutting their doors to dancers wanting to come in at 1.30am and stop serving alcohol at 3am. It was touch and go there for a minute – Sydney’s only under-the-sea-themed Papa New Guinean dancehall almost flat-lined. But never say die, and never surrender - that’s the tiki motto.

Bulletin Place
Three years ago Bulletin Place gave the Sydney bar scene a haymaker it never saw coming. The little DIY attic above a café down near Circular Quay was not where anyone expected to find the city’s best fruit-driven, seasonal cocktail menu. We weren’t used to having a new set of drinks to discover each time we remounted those creaky timber stairs, and we sure as heck weren’t prepared for a raspberry cocktail that would melt our heart instead of making our skin crawl. The Raspberry Calling is almost like a blushing Martini. Gin, dry sherry, lemon juice and bitters gets tinted with fresh berries in ratios that preserve the oakiness of the sherry and the botanical flavours in the gin. The result is distractingly elegant.

Earl's Juke Joint
Bartending is in many ways the study of party alchemy – mixing drinks to lift you up, cool you out and caress your soul if it’s in need of a little TLC. A well made Singapore Sling can send your tongue on a exotic getaway, even if the rest of you has to stay right here and pay the bills; a daiquiri has the power to convince your hips you’ve got the rhythm in you; and an Old Pal can be your best friend after a long day in the salt mines. And there’s nowhere we prefer to pull up a stool and bend the elbow than at the long, sturdy, timber bar at Earl’s Juke Joint.

Vasco
Star Sydney bartenders Max Greco (Eau de Vie) and Luke Ashton (the Roosevelt) have ripped off the shirt-stays and suspenders and traded them in for cut-off denim, trucker hats and a hefty fistful of rock’n’roll. The only tie you’ll see at Vasco is on Ringo Starr. And on closer inspection, we’re pretty sure that’s a cravat. Vasco Rossi, if you’re not an Italian rock’n’roll buff, is one of Italy’s most prolific singer-songwriters. The bar may be named for him, but it’s rockin’ all over the world here. The entire room is a shrine to Greco’s rock’n’roll heroes, from the ‘RIP Kurt’ crucifix to framed pics of the Beatles and the Foo Fighters.

Lobo Plantation
A drink in this subterranean rum bar is as good as a holiday. All that’s ever needed to reset a shitty day or keep a good one rolling is rum cocktails, some jangly tunes and good chat, and you can get it all at Lobo Plantation. In fact, this is the bar we will be spending our staycation in – just roll out a cot under the stairs. In the last 12 months they’ve brought their A-Game to the competitive sport that is inner city drinking, and you, thirsty worker bee, are the real winners.

Monopole
The line between restaurant and bar has gone from a little fuzzy to indistinct, and nowhere is this more so than at Brent Savage and Nick Hildebrandt’s Potts Point wine bar and restaurant, Monopole. You could pop in for a cheeky drink and end up eating the full tasting menu. You could opt for a quick supper that turns into rolling home heavy with biodynamic wines and light on cash. It all depends on what you’re in the mood for.

Mary's
It’s entirely likely that Mary’s is more famous as a burger place than as a bar. People queue for up to an hour just to get in the front door of this slightly scuzzy boozer with a penchant for Slaytanic font (yes, there is a font inspired by the 1980s thrash metal band). Of course only the uninitiated don’t know that there’s often a secondary queue up the stairs for a table on the mezzanine. People really love Mary’s burgers. That hot sandwich turned Sydney’s bar scene on its head – now you can’t lob a brick without hitting someone melting cheese over beef patties and packing them in sweet, soft buns.

The Union Hotel
Down on South King Street the Union goes hard on craft beer. Way before it was the cool, or even fiscally sensible thing to do to have over twenty taps providing frothy thrills of the boutique variety, this spacious Newtown boozer was pouring something way more interesting than lager. Keeping it real for the locals you can expect Willie the Boatman, Wayward, Nomad, Yulli’s, Riverside and Australian Brewery to crop up regularly; Two Birds, Bridge Road, and Feral might represent brews from the greater southern land and there’s even the odd international guest like Sierra Nevada, Anchor and Tuatara to look forward to.

Frankie's Pizza By The Slice
The heart of the business district is not where you’d expect to find an underground heavy metal pizza party, but Frankie’s Pizza by the Slice doesn’t much go in for the expected. The front room feels like a pizza parlour from a movie set, but it’s more Ninja Turtles than Sopranos. Through the looking glass, or rather through the saloon doors, is Frankie’s dark side – no trace of the good Italian boy making red sauce just like nonna used to. The bar and band room is where the spirit of rock has holed up since being ousted from the likes of the Annandale and the Sandringham (Vale, old friends). They’re open until 3am, seven nights a week, which means Mondays can redeem themselves with a set from the famous house band, a frozen Margarita and a tin of Pistonhead lager. Tuesdays is for karaoke, which is followed by two nights of live gigs at the heart of the working week. Fridays and Saturdays hit peak party, but there’s no rest for the wicked on Sundays – just more live bands.

Eau De Vie
There is a dapper gent setting fire to a chopping board in front of our table, and he’s not an arsonist or attempting some sort of Breakfats Club-style fire alarm evacuation – he’s our bartender and the smoke of the cedar board is destined for a glass, following which the rest of our Smoky Rob Rob will be added. The combined forces of Talisker, Lagavulin, rum, vermouth and orange bitters, plus a generous cloud of smoke is like drinking the essence of a really expensive log cabin in the foothills of the Rockies. Blowtorching the serving ware is just the beginning of the dinner entertainment at this theatrical cocktail bar hidden out the back of the Kirketon Hotel in Darlinghurst.

The Wild Rover
Sydney doesn’t downplay its assets. The demand for photos of Bondi Beach is so great that it requires a dedicated gallery; the harbour is the ultimate artists’ muse, and people pay well north of $100 to climb the bridge just for a better view. But Sydney has plenty of secrets too, and one of our favourites is a compact, two-story jungle whiskey bar with an Irish accent hidden in Surry Hills. The Wild Rover is one of those bars that people like to think of as their personal hideout.

The Baxter Inn
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.

Tio's
There is a real and present danger of having too good a time at Tio’s, the Mexican beer hall in Surry Hills with an amazing mescal collection and plenty of salt-rimmed tinnies in the icebox. But the one who brings you low is also your saviour now that they’ve got a snacks menu. Many tiny tacos piled with citrusy chicken, braised pork, or refried beans brightened with fresh corn kernels provide the staying power for another round of forceful Margaritas. For discount cocktail capers beneath the rainbow glow of the fairy lights and luminous chillies strung across the ceiling, look to the menu of classic tequila drinks where $12 buys you a Paloma (tequila, grapefruit, lime soda) or a Tequila Sunrise (have fun getting that out of your head.)

The Hazy Rose
Light beer, low alcohol wine and single serve pre-mixes can really suck the joy out of a night out – but a half-size Martini made with Portobello Road gin is a shot of fun in a novelty-sized cocktail glass, and you can get one at the Hazy Rose on Stanley Street. It’s also the kind of hospitable bar where if you’re off the sauce, they’ll find the most ridiculous pewter flute to serve your tonic water in. That said, you definitely want to drink cocktails up on the first floor of this Darlinghurst terrace. They’ve long been responsible for our favourite Southside in the city, and although it’s not always on the list, the ultimate summer refresher of gin, lime juice and mint is always available.

Palmer and Co.
The underground space is massive but Palmer and Co has a devoted following and stays open late so there’s never stacks of seats to spare. Once you’re comfy it’s time to let the deft, vintage-styled staff take care of you. Cut through all the rich bar food with a Blind Tiger that starts with a foundation of Maker’s Mark bourbon and then adds rich oloroso sherry, nutty house made orgeat, cumquat for a citrus bite and cardamom bitters. It sounds short and potent but is actually served long over ice so all the flavours have room to mingle. Even though you’re deep under the city, there’s still summertime vibes to be found in a classic El Diablo, a tasty devil cloaked in white tequila, blackcurrant liqueur, lime juice and ginger.

The Wine Library
So what if we told you that an orange wine made from no less than eight grape varieties was actually one of the most delicious things in town. Forget the horrors of a king’s cup mixed drink – we’re talking about a wine from Paddington’s booziest learning institution – and they know their shit. You can always opt for a crowd-pleasing drop at the Wine Library, but that needn’t mean it’ll be run of the mill. There are plenty of familiar varieties for the pinot noir devotees, but this is a safe space – get outside your comfort zone and you’ll discover something dynamite. In fact your bartender here is packing a whole cache of awesome recommendations; he’s just waiting for the ‘go’ order from you.

Rockpool Bar and Grill
So, we’ve been writing about this thoroughly realised bar since it opened back in 2009, which in bars years in Sydney, is a lifetime. The towering brackets of shining Riedel glasses, the house-made syrups and sodas, the astounding bar food menu thanks to Neil Perry’s neighbouring restaurant, professional staff operating the shakers – all of it adds up to a benchmark cocktail bar.

Mojo Record Bar
Nothing soothes the spirits like a fresh and smoky cocktail in hand and Beatles tunes on the stereo. And that’s why we keep coming back to this underground bar tucked in behind a record shop – they’ve got the tunes and drinks that’ll turn your workaday frown upside down. It can be disorienting going from daylight to the low candlelight of this backroom bar. It always takes us a couple of seconds for our retinas to readjust so we can find an empty booth to sling ourselves into. Or maybe we’re feeling chatty and opt for a seat up at the bar – super-friendly humans are slinging the drinks here.

The Midnight Special
The Midnight Special’s D.I.Y, rock-basement dive bar look has been properly worn in by now. With any neighbourhood boozer it takes a while to really get that authentic, hard-loved finish. The black paint needs to lose its fresh sheen; the old playbills lining the wall need to peel a little and it takes time to build up a collection of creepy dolls, hula girl ornaments and old soda syphons to tuck in amongst the liquor bottles. Yep, Enmore’s blues and booze den is sitting pretty and she doesn’t lack for devoted company most nights of the week.

The Local Taphouse
The timber floors of the Local Taphouse have been worn smooth by the continuous foot traffic of the parched and the curious over the last five years. The number of licensed establishments spruiking local, boutique and limited-run brews continues to rise, but this corner hotel in Darlinghurst is an old hand at the craft beer game. The gleaming bank of twenty taps behind the ground floor bar still promises some of the frothiest fun to be had in Sydney; a tasting paddle is both an education and a damn good way to spend $17 and an hour or two of your time.

Hinky Dinks
The problem with this super cute Darlinghurst bar is that we want to drink everything. We want the Betty Draper (gin, cucumber and ginger sorbet, lime and ginger beer - so sweet, named for someone so sour) and the Sophomore Slump (rye, sweet vermouth, amaro, bitters). We want a Zombie, though there’s a house rule of only two of these tiki classics a night for good reason - drink more than that and stand near a naked flame at your own risk.

Icebergs
Icebergs can be everything you love about Sydney, or it can be everything you hate. Those with even a slight case of reverse snobbery might accuse this top-shelf Bondi restaurant and bar of being a little private beach club at times. Admittedly, fellow guests do have a tendency to give off a ‘comfortable on any size yacht’ vibe. But letting that get in the way of what could potentially be an epic session would be a mistake. Because when it’s good, it’s very, very good. At the height of its excellence, it gives you the feeling every venue should leave you with: utter refreshment.

Black Bar
Liquid nitrogen in cocktails: it’s a party trick that, thankfully, has gone the way of the marrow shot, the spherification kit and the lychee. That’s not to say N2 doesn’t have its uses. For instance, it makes glasses extremely cold. And here at this classic cocktail bar, they keep a big old canister of the stuff for this very reason. It’s about the only modern touch in a bar that, as a rule, trades in straight drinks served with plenty of class and very little pomp. That could be the Domo Arigato - a full-bodied and nicely balanced shake-up of yuzu, Japanese whisky, spiced sugar syrup and two types of bitters. Or maybe it’s the Royal Cocktail - a riff on the 1930s classic of gin, dry vermouth and cherry brandy that’s altogether unctuous and musky. And the best bit? The team are super nice on top of being super talented.

Eau De Vie
Eau de Vie is hidden in the back of the Kirketon Hotel. The cocktail bar is staffed by a team who are as much about having a good time as they are making you the best damned cocktails you’re likely to drink in Sydney. Don’t drink cocktails? Effervescent bartender Max Greco will lob the top off a bottle of Champagne for you with a sword. Yes, really.

Love Tilly Devine
Ever had a cider that tastes and smells like bandaids (it's actually delicious)? Ever seen a list of Lucy Margaux pinot noir designed to be drunk in different parts of the bar? How about a list of rieslings longer than your arm? No? LTD is the place to try all this and more. Drink here.

Gardel's Bar
Hot! Dog! Sliders! And Pulled! Pork! Sambos! These are the delicious facts of life at Gardel’s Bar - Porteno’s upstairs bar, where tiny beers and Fernet and Coke rule.

The Old Fitzroy
The Old Fitzroy combines cold beers, friendly service and excellent pub grub from Bar H’s Hamish Ingham and Rebecca Lines. The tiny balcony upstairs is the ultimate summer hidey-hole.

121 BC
At 121BC, most of the wines are around $8 a glass, some at $6 and very few above $10. The by-the-glass gear runs the gamut, from Friuli to Abbruzzo, Sardinia and Basilicata - it's all there and we are loving it.

Grandma's
Getting a seat in this tiny bar is pretty much the greatest treat on earth, if you don’t count the friendly service Nuclear Daiquiri or the chicken, cheese and Japanese mayo toastie. 

The Corner House
From the street, this looks just like a restaurant, but take the stairs to level one and you’ll discover cocktails, snacks and good times. Even – or perhaps especially on – say, a Tuesday night. Bondi, it seems, doesn’t have an off-switch. While the cocktail list has remained fairly unchanged for a few years, the drinks are well constructed and the list is divided for maximum ease – first round, second round and third round, taking tipple enthusiasts from aperitif to something appropriate to finish the night.

Shady Pines Saloon
Meet Bobby Carey, Anton Forte, Pasan Wijesena, Alex Dowd, Jake Dimond, Jeremy Blackmore, Scott Frame, Brett Stokes, Max Berry, Mikey Barin, Jason Scott, Chris Stabback and Daniel Mussen. This is the team that makes Shady Pines the bar Sydney can’t get enough of. 

The Victoria Room
Don’t make the mistake of discounting it as a hens’ night hideaway. The Victoria Room is the real deal, combining craft cocktails, incredible bartender knowledge and a beautiful venue.

Eau De Vie
Professor of booze. Human encyclopaedia of arcane drinks. Gentleman bartender extraordinaire. Call him what you will, just call him when you get to the bar

FBI Social
We've pretty much fallen in love with the FBi Social. They’ve taken what was a great location and put put live music back into the Cross, where it'd be missing for too long. 

Shady Pines Saloon
Time does not exist at Shady Pines. No matter what hour you turn up, the bar is dark. It's like entering some alternate dimension: you feel like you've been there for minutes and then, in a whirlwind of fun and country music and great drinks, you're tossed out and it's suddenly midnight. We call it booze heaven.

Eau De Vie
This speakeasy-style cocktail bar is hidden at the back of the Kirketon Hotel. Walk straight through the lobby and out the back to be greeted by a warm, dimly lit room dotted with lounges and tables and a massive bar taking pride of place. Behind the bar you'll find a team of exceptional bartenders led by Barry Chalmers who will pour you just about anything you can think of. 

The Commons
Once upon a time, the Commons was the Pond­- a Pure Blonde-sponsored pop-up bar. It was a cool bar with nice furniture and a fantastic outdoor area. Now it's the Commons - same set-up, different drinks. The bar itself is somewhere you'll want to drink. Wander downstairs to the bar that looks like a 1960s lounge room or stay upstairs and bags a seat at the big outdoor bench. The staff are all super-nice and you're right in the middle of the Surryhurst action.

The Wine Library
Woollahra just got a whole lot more fun with the addition of this neighbourhood bar. The Wine Library is good cheap fun but it gets really busy, really quickly. That means get in early and bags a spot at the bar, or else you'll find yourself standing hunched over your $7 glass of blaufrankisch in a corner or worse, missing out entirely. Make sure to order the boiled eggs and salt and the spiced nuts. 

Four in Hand Hotel
This Paddo local boasts excellent bar food, thanks to chef Colin Fassnidge. The pub menu used to be a different proposition to the adjoining Four in Hand restaurant with a different chef at the helm. But now that Fassnidge has taken over, it's no rest for the restaurant's kitchen and tasty food all round. Don't miss the Sunday roast, which changes every week – great with a pint.

Oxford Art Factory
Oxford Art Factory hasn’t quite made its mind up. Is it a bar, a club, a live music venue or an art space? But that’s exactly why we love it. Your night is pretty much sorted - catch a live gig ranging from up-and-coming to international stars in the big bar without the hassle of having to do the party search once it’s over. Curtains close, beats drop and you feverishly take the dance floor. And when you least it expect it, they’ve decided to throw on another random band in the attached small bar, or a couple of performance artists in the glass cube that sits between the two spaces.

The Shakespeare Hotel
Forget the frocks and cocktails: this baby's about cold beer and tall tales, colourful characters and country charm. The Shakey, as it's affectionately known to locals, is a no-nonsense establishment with a less-is-less-is-more ethos and a classic pub menu. Don't like it? There are plenty of other pubs in the vicinity that'll serve up schmiddies with your change returned on a little tray (shudder).

Bentley Restaurant and Bar
What was then Crown Street's most progressive wine bar has a slick new look is care of Melbourne architect Pascale Gomez McNabb. The light fittings resemble crumpled-up cardboard boxes. Messed-up black mesh acts as a divider between the restaurant and the bar. Speaking of which, the bar is now properly independent from the restaurant. It's a big improvement.

Rockpool Bar and Grill
So, we’ve been writing about this thoroughly realised bar since it opened back in 2009, which in bars years in Sydney, is a lifetime. The towering brackets of shining Riedel glasses, the house-made syrups and sodas, the astounding bar food menu thanks to Neil Perry’s neighbouring restaurant, professional staff like Ryan Gavin and Mischa Bonova operating the shakers – all of it adds up to a benchmark cocktail bar. 

The Local Taphouse
The timber floors of the Local Taphouse have been worn smooth by the continuous foot traffic of the parched and the curious over the last five years. The number of licensed establishments spruiking local, boutique and limited-run brews continues to rise, but this corner hotel in Darlinghurst is an old hand at the craft beer game. The gleaming bank of twenty taps behind the ground floor bar still promises some of the frothiest fun to be had in Sydney; a tasting paddle is both an education and a damn good way to spend $17 and an hour or two of your time.

Café Lounge
Café Lounge is just off Oxford Street and hidden enough to keep out the boozed-up hordes. Behind the wooden doors is your home away from home, with pre-loved sofas and armchairs for those who fancy a quiet tête-à-tête, and tables for larger groups. Menu-wise, it’s all about bottled boutique beers and thin-crust pizzas. Local favourites Stone & Wood, Lord Nelson’s 3 Sheets pale, and Melbourne micro Two Birds’ Golden Ale are among the offerings, alongside Melbourne Bitter cans.

Ash St Cellar
You may well be able to lob a tennis ball from George Street to this quiet pedestrian alley but you wouldn’t know it from the relaxed pace of the punters stopping in for a glass of wine at this little bistro. Decompress out in the breezy laneway or up at the bar where French house featuring atmospheric horns keeps the vibe on a low simmer and devote all your remaining energies to the wine menu. They have an internationally diverse, by-the-glass list that lets you sample the wines of Austria, Romania, South Africa, Greece, Argentina, Germany, the US, Chile and Slovenia, in addition to Italy, France, Australia and New Zealand. And the best part is they offer tasting glasses for half the price of a full pour so you take a little tour without breaking the bank.

The Friend in Hand
The Friend in Hand should be the subject of a Slim Dusty song. It feels like someone uprooted an outback pub and replanted it in the back streets of Glebe, complete with a public bar decked out in more Australiana tat than you can poke a stick at. There’s the famous cockatoo that sits happily at one end of the bar, but he goes to bed at 6pm so if you are keen for a drink with the pub’s avian mascot make it a lunchtime Reschs. A model train set runs along the back of the bar and out around into the foyer passing the street signs, old public notices, black-and-white photos, newspaper clippings, an impressive collection of foreign currency and some mounted taxidermy heads.

Pocket Bar
There was a time when Sydneysiders were starved of good bars and the act of simply existing ensured clientele. That’s not the case these days. Instead, we expect something more than a ‘hidden’ location and booze in a glass – especially if you’re handing over 18 bucks for the privilege. Pocket is one of the city’s original small bars and still offers plenty of reasons to visit. The bar staff are knowledgeable, on the ball and can whip up a cocktail deserving of its price tag.

The Ivy
Justin Hemmes’ multi-level, multi-venue super-club is a Sydney entertainment Leviathan, there’s no denying it. Enter via the Angel Place laneway and saunter past French bar and bistro Felix for a dry Martini and a Reuben sandwich, or head directly across to Ash Street Cellar for a glass of wine and some tapas. Head up the stairs to Palings on level one for schnitzel finger sandwiches on soft white bread and glasses of crisp rosé. Venture even further up and you’ll land at the Ivy Pool Club with its private buttercup-yellow cabanas and sparkling blue pool, like an invitation to peel down to your togs and jump in while holding a pineapple cocktail.

The Beresford
Small bars leaving you claustrophobic? Time to show this big-scale oldie-but-goodie some love. Synonymous with weekend pre-gaming drinks and birthday get-togethers, the Beresford’s massive beer garden remains one of Sydney’s most reliable bar experiences. In a former life it was a famous gay bar, and the gentlemen of Darlinghurst are still well-represented in the crowd (especially on Sunday nights), alongside big groups of blokes guzzling the lager and ladies sipping on jugs of Pimms or mixes of vodka and apple juice (known as the Group Hug jug), St Germain and lychees (called the Secret Garden) or a bottle or two off the bar’s extensive wine list.

Bentley Restaurant and Bar
You might not expect a seriously schmick wine bar and restaurant housed in the original Fairfax building in the heart of the CBD to be all about inclusivity, but the Bentley Restaurant and Bar by sommelier Nick Hildebrandt and chef Brent Savage wants everyone to have a good time. If you’re not here for the full sit-down dining experience that’s A-OK. Grab a table down on the bar level, vanish some exceptional wines by the glass and let the view into the buzzy, open kitchen tempt you to order up some bar snacks like glazed bonito with almond, buckwheat and finger lime, or a fancy prawn cocktail made with macadamia nuts and Mexican cucumbers. Or maybe you just want to pine after whatever they’re hanging in the dedicated charcuterie cupboard sitting right in your sight line. Oh sweet torture, thy name is cured duck breast.

The Australian Heritage Hotel
The Australian Heritage Hotel strikes a comfortable balance between historic tourist stop, and a pub that hard-bitten Sydneysiders still want to frequent. They have zero interest in your traditional Neopolitan pizzas here, preferring a bizarre array of flavours like Peking duck, tandoori chicken, chilli beef and refried beans, smoked salmon and the famous coat of arms pizza with emu and pepper kangaroo meat. Or you could just keep hand and jaw busy with a packet of spiced, local jerky while you peruse the impressive craft beer collection in the double door fridges.

The Hotel Hollywood
The Hotel Hollywood has seen better days. The carpet is a psychedelic mix of colourful swirls on a dark background, designed to mask decades of rambunctious boozing. The wood panelling is chipped and the framed posters are from an age when Hollywood sirens were photographed in black and white, Elvis was breaking hearts and the Melbourne Olympics would have been trending, had hashtags existed. During the week it’s a quiet place to get a schooner of Coopers Green or a stubby of Crown Lager while relaxed electro mixes play at a quiet pulse and the mirror ball keeps spinning.