Until recently, Chippendale was derelict, dangerous no-go zone in Sydney. Taxi drivers avoided it like the plague. But the inner-city district of Chippendale has shrugged off decades of grime and crime to resemble an urban village reborn. Too diminutive to be considered a suburb, this revolutionised precinct, wedged between the Central Railway Station and Redfern might be small in size, but it’s big on reputation.

If you’re planning a fling with Sydney, an urban exploratory through Chippendale will reward you handsomely. Walking south from the Central Railway Station down the wide expanse of Broadway, flanked by faded glories like the old Grace Bros. Department Store, I felt a fizz of anticipation. Shuffling into view was the road sign for “Kensington Street” and the sturdy curved exterior of The Old Clare Hotel. Welcome to the heart of Chippendale.

What is now one of the city’s trending boutique design hotels sprung from the loins of the grimy old administration building for Carlton & United Brewery. The industrial heritage-listed site also houses the fiendishly popular Kensington Street Social, where the chilled out menu is all about Mediterranean share plates, showcasing the best of Aussie produce and wine.

Save some room for a sweet treat and pop into another Kensington Street haunt, Koi, where Reynold Poernomo of MasterChef fame, will exhilarate you with his wondrous dessert bar fare, like Nutella cakes sprinkled in edible, glittery nuts. If you’re up for a five course degustation with gourmet cachet, all roads lead to Automata. Yes, Chippendale has fast emerged as one of Sydney’s premier food districts, without the obnoxious price tags.

The real show-stopper though, is Spice Alley, which has grown from strength to strength in the past couple of years. With a strong tertiary student community within walking distance, Singaporean chef, Alex Lee envisaged the potential of developing Sydney’s first outdoor Singaporean-style hawker centre, serving up Asian street-food cheap eats. Spice Alley is all the more alluring because it’s been developed within pencil-thin lanes that snake around old heritage cottages off Kensington Street.

The courtyards, adjoining the hawker-style food booths are festooned in multi-coloured lanterns, adding to the atmospheric seduction of the aromas drifting in the air.Most stalls offer dishes for roughly $10 like Hong Kong Diner’s pork and century egg congee, Alex Lee Kitchen’s roti canai or Bang Luck’s Thai mussel fritters. Fancy some spicy, flavoursome Malaysian dishes? Old Jim Kee is where to head.

Holy Duck is a great spot too. Open daily from 11am to 10pm, Spice Alley is a multi-sensory winner, plus it’s entirely cashless. Just tap and eat. www.kensingtonstreet.com.au Beyond just being a food hub, Chippendale is also stamping its mark on Sydney’s cultural landscape. In fact, the regeneration of the area kicked off ten years ago with a gallerist, property developer and philanthropist all uncannily converging on this 700 sq metre derelict pocket of Sydney, at the same time.

Nicky Ginsberg, Dr Stanley Querk and Judith Neilson were the powerhouse pioneers behind the staggering arts and culture offerings, coursing through Chippendale today. Over two dozen galleries, from the imposing to the pocket-sized can be found in the precinct. My favourite would have to be Judith’s White Rabbit Gallery which houses the world’s largest collection of contemporary Chinese art, outside the People’s Republic.

Spanning four-levels, this billion-dollar wonderland of colossal sculptures and political pop art is electrifying and unmissable. Remarkably, admission is free. Feeling peckish? The ground-floor Tea House services scrumptious hand-made dumplings and delicate Chinese tea. Other fun stops include aMBUSH and Galerie Pompom, which showcases contemporary works by 18 Sydney and Melbourne artists. Exhibitions change every four weeks.

After enjoying a culture crawl, I called into Freda’s for a restorative drink. This achingly cool yet unpretentious neighbourhood bar has embraced the gallery groove, too. Once a month they unveil a crazy new light installation with sound and video. It’s like Vivid in miniature, in the heart of Chippendale. Despite the gritty bohemian beat to Chippendale, there’s also an unmistakable dose of the shiny and new.

The Central Park development, powered by Dr Stanley Quek, is where necks swivel and jaws-drop. Flanked by gardens and kinetic sculptures, One Central Park is a futuristic 30-storey skyscraper and a symbol of sustainability with a host of green features including a cantilvered heliostat. This gigantic contraption is covered in a series of reflector panels, which automatically disperses natural sunlight.

In the evening the heliostat turns into a giant LED artwork, jutting off the skyscraper. This boundary-pushing building is swathed in vines and vertical gardens, which were designed by the acclaimed landscape artist, Patrick Blanc. What you see at One Central Park is the world’s tallest vertical garden, clad in over 35,000 plants. That’s big brag factor.

In addition to holding over 600 apartments, One Central Park offers distinctive retail therapy within its self-described “living mall”, brimming with independent homeware stores, fashion boutiques and novelty stores like the Japanese two-dollar store, Daiso. Plus Central Park plays host to a cracking outdoors market. www.chippendalecreative.com

If you’re wandering back to the CBD, take a walk along the Goods Line, reminiscent of New York’s High Line. This shared walking and cycling path runs from Chippendale all the way to Darling Harbour, on a partly elevated decommissioned railway line.