If you're planning an autumn fling with Sydney, an urban exploratory through Chippendale will reward you handsomely. Shrugging off decades of grime, crime and decay, this once-dodgy little district, long eschewed by taxi drivers, is a village reborn in Sydney. 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.
Leave 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 top-biller 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.
Beyond just being a food hub, Chippendale is also stamping its mark on Sydney's cultural landscape. Over two dozen galleries, from the imposing to the pocket-sized can be found in the precinct. My favourite would have to be the 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.
After enjoying a culture crawl, I called into Freda's for refuelling. 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.
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.
Reacquaint yourself with Sydney's prized landmarks with a dress-circle view to beat then all. Push the boat out and treat yourself to the celestial perch of InterContinental Sydney, which boasts incomparable vistas across the watery jewels of the Emerald City. Request a room with an Opera House view, or upgrade to Club Intercontinental access, where a wealth of exclusive benefits await, in addition to the offering 270 degree views from the Sydney Harbour Bridge around to Botany Bay.
I enjoyed a lavish breakfast from this lofty perch on the 32nd floor, as Sydney stirred into life. Light refreshments are available all day, while the twilight drinks and canapes service is a twinkling, effervescent affair, from 5pm to 7pm. A plate of freshly shucked oysters and a glass of champagne was the perfect way to salute the setting sun. Whether you're staying in-house or not, another way to marvel at Sydney aloft, on the 32nd floor, is to make a reservation at the Supper Club.
This rooftop lounge and wraparound terrace is pitch-perfect for nocturnal indulgence, with bespoke cocktails, artisan dishes and 27 French Champagnes flowing deep into the night, as you soak up the unrivalled views. The landmark hotel has just announced a $200 million property-wide refurbishment, which will feature unique views of Circular Quay. For best rates and special packages, head to InterContinental Sydney.
Jetstar offers direct flights to Sydney from Auckland, Christchurch and Queenstown and one-stop connections from a number of other New Zealand cities. Flights start as low as $139 one way, Christchurch to Sydney. For guaranteed best fare deals, enjoy a Sydney escape and bag a sizzling deal from Jetstar.
A fun way to fling yourself at Sydney's many charms is to jump onboard the Big Bus Sydney & Bondi Explorer. The hop-on hop-off service features 34 stops and informative commentary, as you tick off the sights on the double decker open-top buses. I love the Blue Route, which threads its way east of Paddington, with memorable stops at Double Bay, Rose Bay and Bondi Beach. Book your tickets at Big Bus Tours.
Mike Yardley is our Travel Correspondent on Jack Tame Saturday Morning.