First published on 7 Sep 2010. Updated on 5 Apr 2011.
Best for: Scheming over s'ghetti
Plot your next corporate takeover or political coup over a bowl of penne Bolognese at Machiavelli. Every heavy hitter has eaten here at one time or another, from "Aussie" John Symonds to Julia Gillard – each with a larger-than-life photo on the wall to mark the occasion. The restaurant's been open 22 years now offering the likes of steak Diane (a Machiavelli signature) and crepes Suzette. The dining room is 95 per cent older-man-in-suit. Get power dressed, grab a seat in the corner and start scheming. 123 Clarence St, Sydney 2000. (02 9299 3748).
Best for: A cheap date
You can eat here for under $15, there's excellent gelati for dessert, and if you've taken a punt on a date you're not sure about, it's loud enough to hide the awkward silences. Bar Italia is one of the busiest places to eat in Leichhardt, with lines out the door and a room full of hungry punters squished together on benches and tables. Out the front, crowds clamour for cones piled high with gelato, while out the back it's all about the baked cannelloni stuffed with ricotta and covered in tomato sauce. 169 Norton St, Leichhardt 2040. (02 9560 9981).
Mamma Maria Upstairs Restaurant
Best for: Local celeb spotting
A big favourite with Sydney musos, povvo students and hungry locals (seriously, the food here is huge), this secret Sydney red saucer is great, cheap fun. You'll need to enter a narrow staircase, risking life and limb to get to the restaurant upstairs, which is filled with friendly old Italian waiters who don't mind taking their time getting your lasagne. The beers are cheap, everyone's having a good time and there are at least four pubs in tottering distance for afters. 239A King St (Cnr Church St), Newtown 2042. (02 9516 4428).
Best for: Going just to say you've been
The legendary Grotta Capri, with its three tonnes of sea shells stuck all over the walls inside and out, has made star appearances in the likes of Muriel's Wedding, White Collar Blue, Wildside and Underbelly 2. And no wonder – it's a restaurant experience like no other. Dining at the Grotta means being bathed in an eerie blue glow cast from the many fish tanks set into the walls and the fairylight-flecked stalactites that jut from the ceiling alongside fake lobsters (Aussie ones, no less) and giant clams. If you’re into karaoke, the Grotta have a huge song selection on Fridays and Saturdays with two versions of Guns ‘n’ Roses’ Welcome to the Jungle. Drinks-wise, you’re best to stick with beer. 97–101 Anzac Pde, Kensington 2033. (02 9662 7111).
Bill and Toni's
Best for: Free cordial!
The late Bill Chiappini learnt to make coffee in Kings Cross after emigrating to Sydney from Sicily in 1957. When his boss lost his café in a high stakes poker game, Bill was unemployed until Luigi Coluzzi offered him a job and soon, the means to buy Bill & Toni's (then San Siro) in 1964. This East Sydney stalwart has been feeding hungry Sydneysiders ever since. Sit at one of the outdoor tables and nurse an espresso, order the veal parma, or hit the carbs with a big bowl of pasta - every meal comes with free bread and orange cordial. 72-74 Stanley St, East Sydney 2010. (02 9360 4702).
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