What to see and where to be seen

A seasoned hedonist should never have a massage before a night of debauchery, but that's exactly what I've gone and done. Smothered in essential oils from a pampering session at the Shangri-La hotel's Chi the Spa (00 61 2 9250 6000; shangri-la.com), I feel more placid than party-girl, as I float upstairs to my suite. It's almost too tempting to wrap up in a bathrobe, order room service and guzzle the mini-bar dry. But gazing out at the glittering harbour view, Sydney's nightlife beckons – and Australia's sassiest city is a mistress who waits for no one.

Anyone who pooh-poohs Sydney's nightlife should think back to the last time they visited. Since 2009, the stranglehold on licensing laws has loosened; these days it seems barely a week passes without another bar opening.

The so-called "small bar" scene is flourishing, and a short taxi ride away, my friends and I are hanging with the cool kids at one of the city's hippest venues: Grasshopper (00 61 2 9947 9025; thegrasshopper.com.au). It's a slip of a thing wedged in a former derelict laneway now heaving with stylish twenty- and thirtysomethings, where cocktail names are replaced by numbers.

I keep a straight face when I ask the bartender whether he likes number twos. Turns out he does – and so do I. After quaffing two, eight and 21, we steady ourselves to walk to The Ivy (00 61 2 9240 3000; merivale.com), a multi-bar-and-restaurant ode to pleasure-seeking that culminates in a rooftop pool.

We schmooze our way past the clipboards and head for the bar. Here, aside from posturing, posing and trust-fund boasting, it's all about the outfit – or lack thereof. Tsk-tsk, did you forget your swimsuit? Fear not, they sell them at the bar. The place to take in the splish-splashing exhibitionists is the glamorous, invite-only Ivy Penthouse bar on level six. The split-level haunt takes in a sexy, circular leather lounge and a dance pole that lowers from the ceiling over the marble coffee table. The sanctified few can overlook the pool shenanigans below from the comfort of the Jacuzzi on the balcony – Dom Pérignon in hand.

It's all exceptionally classy but our behaviour after a few Negronis is anything but, so we take a cab to Burton Street for further libations at The Commons (00 61 2 9358 1487; thecommons.com.au), Pocket (00 61 2 9380 7002; pocketsydney.com.au), and lastly Shady Pines Saloon (shadypinessaloon.com), a Western-themed dive bar where the whisky is served straight up and the bar is made for slouching.

Next, it's time for sustenance, so we head to Duke Bistro (00 61 2 9332 3180; dukebistro.com.au), an edgy eatery headed up by formidable young chefs who flip a respectful bird at bland gastronomy: try kingfish gin-and-tonic sashimi or quail with coffee and pistachio. After dinner, we walk past Oxford Street's flamboyant gay bars to Hunky Dory Social Club (hdsc.com.au), with its painfully beautiful crowd.

Fast forward and it's nearly 2am. Our lubricated bellies are baying for a second feed. We hail a cab to Golden Century (00 61 2 9212 3901; goldencentury.com.au), the legendary Chinese restaurant where service is surly at best – but there's a reason the sprawling restaurant is packed out, even at 3am. The seafood is sublime and the gai-lan so garlicky that hair sprouts from the chest with each chopstick-full.

At 10am the following day, the sun is mocking us. What to do with this hangover? Nothing beats immersing a puffy face into the brisk Bondi surf. The deal is sweetened with a Campari and fresh orange at North Bondi Italian Food (00 61 2 9300 4400; idrb.com). However, the way my stomach is feeling, waves and cocktails are foe, not friend, so we go east.

Nielsen Park is a harbour-facing beach favoured by Sydney's fashionable eastern suburbs set. It boasts a great little café (00 61 2 9337 7333; nielsenpark.com.au) serving knock-out eggs Benedict. There's little else to do other than work on our tans, cool off in the water... and plan the next night's activity.

A Hedonist's Guide to... (Hg2) is a luxury city guide series for the more decadent traveller. For more information, see hg2.com