Sydney's Chippendale is an inner-city suburb with a difference: it's home to the world's tallest vertical garden; a gallery with one of the country's most significant collections of contemporary Chinese art; both street food and fine dining options; and a one-of-a-kind place to stay.  

Street food, fine dining and a wine or two

Whether you're after bread, brunch, a quick noodle soup or a multi-course fine dining meal with matching wines, Chippendale has something for all appetites. The suburb's hub is Kensington Street, a labyrinth of old homes turned into gin bars, patisseries, snack stations and cutting-edge restaurants. Highlights include MasterChef-style patisserie by Reynold Poernomo at Koi Dessert Bar and high-end European menus at Olio (Sicilian cuisine) and Gavroche (French). For a unique cellar door experience in the city, drop into Handpicked Wines for a wine tasting with some of Australia's best cheeses and some international additions too. On the casual side, check out Kensington Street's Southeast Asian-inspired Spice Alley, which sees hawker-like stalls distributing everything from ramen to roti canai with a side of curry and sambal.

In the neighbourhood's backstreets pick up a Persian love cake to take away, settle in for a sandwich served on seeded ciabatta at Brickfields Bakery, or nab a seat in the sun at La Herradura Coffee Stable for hearty Colombian fare and coffee made with Colombian beans. You'll need to book ahead for Kindred, a neighbourhood Italian restaurant with a strict make-everything-in-house philosophy and Ester, one of the best modern Australian restaurants in Sydney (chef Mat Lindsay was Gourmet Traveller's Chef of the Year in 2018). For a more casual drop-in meal and drink, head to the Duck Inn Pub and Kitchen for beer or a roast in the sunny, pet-friendly courtyard.

A one-of-kind kind stay

Tonkin Zulaikha Greer Architects' striking reinvention of The Old Clare Hotel has won multiple international architecture and design awards for incorporating the heritage of the original County Clare Hotel and the old Carlton & United Breweries administration building, with modern sophistication in both its public and private spaces.

Among the 62 rooms in the heritage-listed building is the C.U.B. Suite, which sits in the old boardroom of the brewery. Opulent original features such as chandeliers, timber panelling, even the executive bathroom – have been given a stylish restoration and the hotel's dining and drinking options are just as impressive. Longshore is a sustainable seafood restaurant from the acclaimed team who used to run much-loved Newtown restaurant Hartsyard, and Clare Bar reimagines Australian pubs with the style of a boutique hotel bar. Add on to that a rooftop poolside bar that offers a grand view of the city and the vertical gardens of the One Central Park building next door.

Award-winning architecture and sustainable design

Chippendale is home to the world's tallest vertical garden. Thousands of shrubs, vines and flowers cascade off One Central Park – creating a 'green screen' around the award-winning, sustainability forward building. For more eco-friendly design in Chippendale, book a tour of sustainability campaigner Michael Mobbs's off-the-grid 19th-century terrace. The tour guides people through the sustainable home, which generates its own electricity and draws on collected rainwater. There's also the option of adding in consultation on how to make your own residence more environmentally friendly.

One of the most unique art galleries in Australia

A few blocks from One Central Park is White Rabbit Gallery, which showcases one of the world's most significant collections of Chinese contemporary art. Owner Judith Neilson has acquired more than 2,000 works over several decades with the gallery, a converted former Rolls-Royce depot, exhibiting a regularly rotating range of styles and artists. After browsing the collection, which is free to enter, head to the White Rabbit Tea House. It's adorned with a striking cluster of suspended birdcages and serves dumplings and an extensive list of Chinese and Taiwanese teas.

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