First published on 22 Jun 2011. Updated on 26 Apr 2012.
The Australian Heritage Hotel
You'll meet everyone from devoted locals to overseas converts and puffed-out BridgeClimbers here. There's more to this 95-year-old pub than the Dundee-esque cavalcade of kangaroo, crocodile or emu pizza - it's got some of the richest history, and best the outdoor seating in Sydney. A champion of the Aussie micro-brewing industry and host of an annual beer festival, the Australian boasts eight local brews on tap as well as plenty by the bottle (Fish Rock, Byron Bay Ale, Pigs Fly and Redoak) and if you're lucky you might even find yourself a new favourite. The Australian packs a wine list too, with lots of Aussie drops by the glass. An essential stop-off on any Rocks pub crawl. 100 Cumberland St, The Rocks 2000. (02 9247 2229).
At Wine Odyssey there's an abundance of premium Aussie wines from independent producers. Opt for one of the intimate tasting rooms and receive complimentary bites to eat as you trawl through the list and try some of the best wine Australia has to offer. The palate takes firm centre stage here but the other senses are set for stimulation thanks to the interactive film of the Wine Theatre and the remarkable Aroma Room. 39–43 Argyle St, The Rocks 2000. (1300 136 498).
This is one of the few pubs left in the Rocks dating from before World War II and it shows. This beautiful, heritage-listed pub looks straight over to the Opera House and Circular Quay and is one of the few pubs left with a proper roof garden and bar to match. Renovations are currently underway so you may have to pop next door to the Australian for a sneaky schooner, but fear not, the Glenmore will be back in action soon enough. 96 Cumberland St, The Rocks 2000. (02 9247 4794).
The Hero of Waterloo
The Hero is one of Sydney's oldest pubs, constructed using convict labour and built with hand-hewn Sydney sandstone. And the years have done little to diminish its charms. Not that it's been painstakingly preserved, mind you (few 19th-century public houses had pokies, for one thing), but it's certainly a pub that's sure of itself. It has high-profile fans too – Paul Keating among them. Come Saturday nights there are singalongs around an old piano, maintaining the romance of a bygone age when drunk punters were tipped down a trapdoor out back and awoke to find themselves enlisted in the Royal Navy. They've discontinued the practice, but best be wary... 81 Lower Fort St, Millers Point 2000. (02 9252 4553).
The Lord Nelson Brewery
Sydney's first boutique brewery (they started brewing back in 1986) has six different brews in their holster including three ales, two bitters and a porter. The pub itself is all high ceilings, cool sandstone, blazing hearths and convict history. You can watch the brewing process via views of the fermentation tanks or plonk down outside and watch Millers Point. Order all the beers on tap and conduct your own tasting session. 19 Kent St, The Rocks 2000. (02 9251 4044).
The Club Bar
If log fires, mahogany, overstuffed armchairs, Dean Martin and a nip of aged, peaty whisky sounds like something you might be interested in, you could do worse than pull up a stool here. The classic cocktail list boasts all drinks short and tall, including much-loved regulars like Martinis and Aviations as well as more arcane drinks like the Martinez, Monkey Gland and White Lady. The bar takes precedence in the space and there are nice touches such as spiced nuts at the bar and a humidor filled with rare cigars – though with the new smoking laws you'll have to step outside to enjoy one. 7 Hickson Rd, Millers Point 2000. (02 9256 1877).
In the wise words of Brendan Behan, Guinness makes you drunk. And the Merc serves plenty of it. Refreshingly, this place isn't overflowing with Irish memorabilia, but it's nonetheless constantly packed with people hailing from Eire. The big all-wood bar is a stunner. 25–27 George St, The Rocks 2000. (02 9247 3570).
Fortune of War
If you manage to squeeze in the door (it's tiny and often packed), you'll find a mixed bag of punters from suits to tradies to tourists. This is generally a no-nonsense bar and the stern (though friendly) bar staff and their handlebar moustaches take no schtick. There's a respectable selection of Aussie wines, but really, if you're here, you're here for a beer. There are 15 on tap including VB, XXXX, Reschs and all the Coopers of the rainbow, as well as Asahi, Kirin and the lemon-lime infused Barefoot Radler. 137 George St, Sydney 2000. (02 9247 2714).
Wildfire's long skinny room is mostly taken up by a bar stocked to the gills with the world's best booze - rare tequilas and rums line one shelf and another is spilling over with any gin you care to mention. From Dr Jerry Thomas to David A Embury, the breadth of drink knowledge behind this bar is impressive. There's also a huge wine list if cocktails don't send you weak at the knees (or wallet), with an excellent range of Champagne and a primo vino list spanning from gewurztraminer to Burgundy. Circular Quay West, The Rocks, Sydney 2000. (02 8273 1222).
A cobblestone path leads you into one of the coolest courtyards in Sydney, which in the early days of settlement served as an unloading dock for tall ships lugging in and out of the Argyle Storehouse. On late-summer evenings, this corral is swarming with over-excited patrons in full party mode. Watch the bouncers, though; they take no lip and won't even blink at turfing you if you misbehave. 18 Argyle St, The Rocks 2000. (02 9247 5500).