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Old Fitzroy Hotel
A slice of London's Islington in the back streets of Woolloomooloo, this is a proper theatre pub but also a decent old-fashioned boozer in its own right. The little balcony is unbeatable on a hot steamy night and there are airy street-side tables. Wednesday night trivia is a hoot.
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Opera Australia
Opera Australia is a big player on the Sydney arts scene, based at the Sydney Opera House and at Melbourne's State Theatre.
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Opera Bar
Lapping on the harbour's edge under the low-slung Opera House eaves, this sexy, curvilinear room grabs everyone from snap-happy tourists to business lunchers and tutors them in the ways of sophisticated boozing. DJ's play jazz, soul and funk nightly; bridge views play 24/7.
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Orbit
For the price of a trip up Sydney Tower you can get four happy hour cocktails at this 47th-floor lounge bar at the top of Australia Square. Sink into an Eero Saarinen tulip chair under the glow of an Alex Noble lamp and watch Sydney spin around far below. No thongs, shorts or singlets allowed.
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Oxford Hotel
The bustling corner locale can't be beat, especially if you land a patio table on the square. Downstairs it's the hard-core manly gay bunch, while on the second floor Gilligan's cocktail bar attracts a fancy mixed crowd of bohemians. The top floor is open weekends only, and definitely worth a stop.
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Paddington Inn Hotel
On the outside, this pub is large, popular and pretty - but it's surprisingly swanky on the inside. The airy window seats are gold, especially when the nearby Paddington market is in full swing. The food is fancy and the cocktails elaborate. And if you need a change of pace, Oxford street's more rowdy (read: gay) bars are a stone's throw west.
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Palace Verona
This cinema has a café and bar, useful for discussing the artistic merits of the latest non-blockbuster flick you've just seen. Other Palace cinemas include Palace Academy Twin, home of the Mardi Gras Film Festival, and Palace Norton St.
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Peppermint Lounge
Remember when getting into a nightclub meant guys needed a nice collared shirt and leather shoes? Nothing's changed here, and the spiffy young crowd love it. Curl into the padded booths seemingly carved out of the wall by a melon-baller and order a cocktail while listening to deep house with an electro and hip-hop flavour.
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Performance Space
This avant-garde arts project has recently relocated to Carriageworks - a fascinating group of huge Victorian-era factories that were part of the Eveleigh Railyards - where they have a shed devoted to installation and multi-media art as well as performances.
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Pinchgut Opera
This relative newcomer stages one intimate, often neglected, chamber opera every December at the City Recital Hall.
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Pontoon
One of the most popular drinking dens at Darling Harbour, offering water breezes, high-tech atmosphere and cool sounds. There's dancing on weekends, when DJs lay down the R&B and hip-hop and live jazz chills the air on Sunday afternoons.
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Q Bar
With more reincarnations than Cleopatra over the years, this funky and eclectic joint (located in the Exchange Hotel) has DJs playing nightly. Weekends means house and dance music, but if you're not into that there's always the pool table and cocktail bar. On Fridays and Saturdays this place should be more accurately named Queue Bar.
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Redoak Boutique Beer Café
Ever beer-haters will find something drinkable here, whether it's a honey ale or Belgian chocolate stout. Redoak has been the most awarded brewery in the Australian International Beer Awards for three years running. Try a beer and food tasting - four beers individually matched with finger food (chose from meat, vegetarian, seafood, cheese or dessert) for around A$20 .
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Rose of Australia
A gorgeous old corner pub, recent renovations haven't dinted the tiled front bar's charm one iota. Locals of all persuasions hang out here, catching the afternoon sun at the streetside tables, a footy game on the big screens, a meal upstairs or the live performers on Wednesday and Friday nights.
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Ruby Rabbit
If you can make it past the door Nazis, Ruby Rabbit offers a sumptuous, stylish trio of long thin bars that might have been designed by Liberace. There's no room for pretension when the decor's this camp. Entry to Versailles-inspired De Nom on the top floor is only by reservation, membership or referral.
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Sandringham Hotel
A minimal amount of money (or none at all) will score you a live music fix at this intimate venue where God comes for a tipple, according to a song by local legends The Whitlams. There's a small beer garden, free internet and three-hour happy hours.
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Slide
Slide inside Slide, a gorgeously converted banking chamber where a colourful crowd of sexy gays and straights shimmy across polished concrete between plush booths and the central bar. If the sound and vision overwhelms, spy yourself a candidate from the mezzanine.
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Slip Inn
This historic complex offers plenty of choice if you're looking for bars, pool tables, a beer garden or dance floor. Friday night is breaks night at the Chinese Laundry nightclub, while Saturday is Laundry night, featuring a changing roster or local and international DJs.
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Soho Bar & Lounge
The beautiful Art Deco Piccadilly Hotel is a dark, relaxed establishment whose smooth leather lounges have felt the weight of Keanu Reeves', Nicole Kidman's and Ewan McGregor's celebrity booties. It's rumoured to be where Kylie met Michael Hutchence. Soho is actually the upstairs cocktail bar (evening's only), but the ground floor Piccadilly Room is just as elegant.
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Sol's Deck Bar
When you drag your bones out of bed at whatever pm, boot it down to Sol's for a beer, some tapas and a perv over Taylor Sq. The cocktail bar fires up later on with resident DJs Sista P and Renae Stanton. Lipstick ladies love Friday night's 'Bitch' session.
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Speakers' Corner
Recline on a patch of lawn in front of the Art Gallery of NSW and listen to religious zealots, nutters, political extremists, homophobes, hippies and academics express their earnest opinions. Some of them have something interesting to say; most of them are just plain mad. Either way, it makes for an interesting afternoon. BYO soapbox.
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St George Open Air Cinema
In the city, the Open Air Cinema offers outdoor summer cinema on a massive screen with surround-sound, plus swanky food and wine. Bookings essential.
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Stables Theatre
In the 19th century this place was knee-high in horse dung; now it's home to the critically acclaimed Griffin Theatre Co, dedicated to nurturing new writers and performing experimental works by contemporary Australian playwrights. Book online, by phone or at the box office an hour before the show.
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Star City Casino
This huge casino, theatre, retail, restaurant and hotel complex is on the waterfront in Pyrmont, on the northeastern headland of Darling Harbour. Decor is best described as 'Disney-meets-Outback', and really is a sight for sore eyes. There's a hundred and one ways to gamble here, and it can get packed on weekends.
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State Theatre
The beautiful, 2000-seat State Theatre is a lavish, gilt-laden, chandelier-dangling palace. It hosts the Sydney Film Festival , concerts, comedy and the odd musical. For more details see their website.
