Sydney's eye-popping setting, sprawled around one of the world’s best looking harbours, keeps tourists slack-jawed. Locals, however, are more likely to be found ogling fashion-forward labels in Paddington’s glam boutiques or enjoying cocktails in party-hard Darlinghurst – the laneways buzz with brilliant bars, boutiques and restaurants. Explore arty Newtown, ramble around the Rocks, take a boat trip or two and set off on a scenic coastal walk. Beyond the harbour city lie the Hunter Valley’s vineyards, the staggeringly beautiful Blue Mountains and – eight hours away by car – Byron Bay’s laid-back beaches.

Spotlight on: Sydney Harbour

There’s more to Sydney Harbour than the name suggests: we’re talking 240 kilometres of dazzlingly photographic shoreline, home to lush gardens, glittering beaches and peaceful patches of bushland. Of course, some of the city’s biggest draw-cards also call Sydney Harbour home – the iconic Opera House and the vertiginous Harbour Bridge, for example.

Smith insider tip #1

Eat at... Ester, whose $65pp banquet menu will have you cantering from one Italian delicacy to another – we’re talking fat, buttered prawns, smoky morcilla sausages and dazzling desserts.

Don’t miss... The crowd-pleasing ‘Three Milks’ pudding: an ambitious confection of ricotta panna cotta, dulce de leche and sour yoghurt mousse, with olive crumbs for added crunch.

Smith insider tip #2

Drink at... Golden Age Bar, attached to Surry Hills’ glamorous Golden Age Cinema. The subterranean space dishes up potent classic cocktails, served with 1920s-style insouciance.

Don’t miss... The witty, film-inspired food specials: Fellini or Spielberger toasties, John Candy sweet boxes, a Steve Zissou-inspired anchovy dish and the ilk.

Smith insider tip #3

Sleep at... The Old Clare, a boutique basecamp with a boozy past (the hotel is housed in a former student pub and what was once the administrative HQ of Carlton United Breweries). The love of beer endures: there’s a bar kitted out in brown-hued light panels that nod to the autumnal hues of beer bottles; you can also expect a solid selection of craft beers and original features, including grungy band posters and the Brewery HQ’s intact boardroom.

Don’t miss... Clare’s brilliant on-site restaurants, courtesy of top chefs Jason Atherton and Clayton Wells.

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