Chippendale

Today's darling of urban reinvention, the once gritty suburb of Chippendale (Chippo to the locals) is tucked just behind Sydney’s Central Station. Instantly recognisable by the sustainable skyscraper that towers above - Central Park - it's actually covered by the world's tallest vertical garden. It used to be an enormous brewery surrounded by slum in Sydney’s earliest days, before visionary Dr Stanley Quek transformed it into one of Australia’s most exciting urban renewal precincts. Go for a stroll to admire it from up close, then wander around the surrounding outdoor sculptures, including Turpin + Crawford's minimalist Halo.

As you explore, look out for White Rabbit (free) gallery, radically transformed from an old knitting factory and now housing the world's largest and most significant collection of contemporary Chinese art outside China. The cafe serves fabulous dumplings and a wide range of Chinese and Taiwanese teas. While you're in the neighbourhood, check out its impressive street art at the upstairs Goodspace gallery at the Lord Gladstone Hotel. If you would rather explore with a local guide, take the Chippendale-Redfern Tour with Culture Scouts, which combines visits to art galleries and shopping boutiques with the insider story on how this area evolved.

For a casual lunch, feast on Asian street food at contemporary outdoor foodie destination Spice Alley, where permanent stalls are lined up across the facade of Kensington Street's heritage terrace houses and a small lantern-lit courtyard buzzes with happy diners. The stalls are run by veterans of some of Sydney's most popular South-East Asian restaurants, specialising in everything from Malaysian cuisine to Hong Kong fast food. For cutting-edge dining, Ester offers a sublime experience in a pared-back space with an open kitchen, while LP’s Quality Meats is the place to go for smoked and cured meats.

And for all your bread, pastry and coffee needs, head to Brickfields, which is primarily a bakery and takeaway coffee bar. If you’re hoping to stay locally, book into the edgy, boutique Old Clare Hotel, cleverly created from the historic bricks, concrete and timber of an old pub and the adjacent Carlton United Brewery Administration Building (they’re joined by a glass and steel atrium). Speaking of breweries, there are pubs for all persuasions in Chippendale. The Rose Hotel is popular with the university crowd as well as locals watching the rugby league. The Duck Inn Pub & Kitchen has been reimagined with an airy, almost beachy decor, complete with board games, a packed bookshelf and a sunny beer garden with umbrellas and picnic tables. Zigi’s Art Wine Cheese Bar has an interesting concept while they wait for their liquor licence: it is operating as a bring your own (BYO) wine bar while it supplies the cheese.

Darlinghurst

With a past as colourful as the rainbow flags that wave across Darlinghurst, this inner-city suburb has come a long way since being the epicentre of Sydney's underworld during the early 20th century. Now packed with designer boutiques, impressive galleries, lively coffee houses and a flourishing gay pride culture, the greatest danger is over indulging.

Speaking of, you cannot visit Darlinghurst and not sit at the original shopfront of the (now international) Bills franchise. During the 1980s and 1990s when Darlinghurst underwent its urban renewal transformation from a red-light district to a cosmopolitan inner-city hub, Bills was one of the first new businesses to open and is still running to this day. There have been a slew of new cafe openings since then including the local favourite Latteria, one of Sydney’s tiniest venues with a famously good focaccia menu. Messina Gelato is another famous name that first opened in Darlinghurst and has since opened shopfronts all over the country. Don’t let the queue put you off, the Dulce De Leche is something everyone should try at least once. For dinner, be sure to arrive early for a coveted seat at Buffalo Dining Club, an Italian inspired eatery serving up freshly imported mozzarella with simple fresh sides and pasta served out of giant hollowed-out wheel of pecorino.

Situated less than two kilometres (one mile) southeast of Sydney's city centre, Darlinghurst is regarded as the heart of Sydney’s burgeoning small bar scene. Love Tilly Devine is a laneway wine bar with a 300-strong wine list, and just a 10-minute walk away is Eau de Vie, a 1920s-inspired bar complete with moody lighting and the best whisky cocktails in town. Shady Pines Saloon is a local favourite famed for its cowboy fit out, craft ales and bowls of peanuts.

Stepping away from small bars entirely is Oxford Art Factory, the home of Sydney hipsters and a venue for some of the biggest touring musical acts. Darlinghurst is synonymous with gay pride, as seen across the neighbourhood with rainbow flags, rainbow street art (visit Taylor Square) and one of the biggest events on the local calendar, the Sydney Gay and Lesbian Mardi Gras. Capturing the imagination of Sydneysiders every year with three weeks of fairs, exhibitions and parties, it culminates with a dazzling, world-famous parade along Oxford Street.

As with the bar scene, there is an equally strong custom-made or boutique flavour clear in the local accommodation offerings. The Kirketon Hotel houses just 40 guest rooms, each featuring modern conveniences and luxurious furnishings. On the cusp of Darlinghurst and Kings Cross, just behind the famous Coca-Cola billboard, is the Larmont Sydney by Lancemore, with 76 modern rooms each comprising a plush king-sized bed, sleek decor and an in-room iPad to serve as your personal concierge.

Sydney's beaches

Welcome to the lifestyles of (Sydney’s) rich and famous, all located in a pocket that begins at the eastern border of the city and ends at the coastal break of the Pacific Ocean. Just a 15-minute drive from the city, the Eastern Suburbs hold some of the country’s most expensive real estate, designer boutiques, top-end dining and drinking destinations, and of course some of the very best beaches in Australia.

If you have just one day to see this neighbourhood, start as the locals do with a sunrise surf at the south end of Bondi Beach. Let’s Go Surfing offers a range of private and group lessons run by professional surfers. Or better yet, watch the action from a Bondi landmark, Icebergs Pool, open to the public each day apart from Thursday when it closes for cleaning. Follow this up with a jog along the Bondi to Coogee coastal trail, a six-kilometre (3.7-mile) clifftop path that links up all the main beaches. If you're in town during the annual Sculpture by the Sea outdoor art exhibition, you'll see this route transformed with temporary art installations. Once you arrive at Coogee, cool off with a dip at the heritage-listed tidal swimming pool, Wylie’s Baths, and then grab a quick juice or smoothie from Coogee Pavilion before making your way to Three Blue Ducks in Bronte for a delicious, sustainably sourced brunch. Be sure to leave some room for a freshly-baked pastry from the famous neighbourhood bakery Iggy’s Bread before walking off the calories with some retail therapy on Bondi’s Gould Street, home to Australia’s premium boutiques. Around the corner is the local gallery Aquabumps, where surf photographer Eugene Tan showcases his famous snaps of the beaches.

Each year Bondi hosts a diverse calendar of festivals and events like the annual kite-flying extravaganza Festival of the Winds held each September, and from January to February Openair Cinemas screens the best new releases and cult classics on its outdoor movie screen. During winter (June to August), test your legs on the ice-skating rink at Bondi Winter Magic festival or in the Sun-Herald City2Surf, a 14-kilometre (8.7 mile) fun run that attracts more than 80,000 participants.

End the day with a bucket of fresh prawns and a cocktail jug at the Bucket List as you watch the sun set over Bondi Beach. If you’re looking to stay locally, the QT Bondi has a range of beach-facing rooms with décor that’s as bright as the neighbourhood.

Manly

Nestled between a tranquil beach on one side and the popular Pacific Ocean surf beach on the other, the laid-back character of Manly seems a thousand miles from busy Sydney, yet it’s only a ferry ride away. Whether you like to feed your sense of adventure, your tummy, your curiosity or simply sit back and take it all in, this beachside town has a little of something for everyone.

Manly is easily reached by ferry which run regularly from Circular Quay near the Sydney Opera House. The 30-minute ferry ride to Manly provides undoubtedly one of the best views you’ll get of a thriving harbour and the many beautiful harbour beaches along the way. One of the first things you’ll notice when you arrive is the bustle of Manly’s restaurants and bars. Soak up panoramic harbour views at the Manly Pavilion, relax just off Shelly beach at The Boat House for a long leisurely brunch, or for something a little different, create your own platter of delicious meats, cheeses and pickles at Cured - it’s like a little bit of NYC found nestled in bustling Market Lane. The Four Pines Brewing Company is a craft beer lover’s delight, while Manly Spirits Co. serves up premium gin and botanical vodkas infused wtih native ingredients.

From one end of Manly beach to the other, you’ll find an array of water activities to suit the whole family. Try a stand-up paddle boarding or kayaking tour. Manly Kayak Centre will guide you around exclusive beaches and stunning scenery and even offers a picnic. Everything is provided and it’s perfect for beginners. Learn to surf in Queenscliff (which is at the northern end of the beach) with Manly Surf School or perhaps an amble along the tree lined corso to the south end where you can swim and snorkel in the calm waters of the beautiful Shelly beach; it’s a great place for kids.

If exploring if your thing, the Manly to Spit Bridge coastal walk meanders around the harbour foreshore through some of Sydney’s most stunning scenery and bushland. The whole walk is 10 kilometres (6 miles) however it’s broken up into a series of 1-2 kilometre (0.6 – 1.2 mile) short walks which are well sign posted with direction and information spots. Observe the bush and coastal wildlife including whales during the migration season, learn about Australia’s colonial history, take in the views from spectacular vantage points and enjoy a well-earned dip in one of the many off-the-beaten-track harbour beaches. Join EcoTreasures, an Advanced Eco Tourism certified experience, for a guided snorkel to spot native marine life. Your guide will also educate you about local wildlife, which changes with the seasons. Plan a tailored tour to discover a range of coastal eco experiences. If stretching out on the golden sand for some Vitamin D is more your style, there’s 1.5 kilometres (0.9 miles) of it to choose your perfect spot from.

Surry Hills

Once home to Sydney's rag trade, this buzzing inner-city neighbourhood has converted its industrial warehouses into swanky gallery spaces and million-dollar apartments. On the southern reaches of Sydney's city centre, jacaranda-lined streets, upscale boutiques and restored terrace houses contrast with edgy dive bars and colourful characters.

Crown Street is undoubtedly the retail gem in Surry Hills, with vintage shopping like TITLE for everything music related, and Cream on Crown which offers a chic edit of upcycled clothing. More elegant than eclectic, Collector Store is akin to a gallery display of homewares and fashion, on par with The Standard Store, which stocks an impressive range of handpicked fashion and lifestyle pieces.

But the area's most defining trait is an ever-changing food scene. It's home to some of the best coffee in the city, like Artificer Coffee whose food-free coffee menu is as minimalist as its floor-to-ceiling American oak interior. If you’d like your coffee with a side of brunch, check out longstanding favourites like Bourke Street Bakery, Bills and Four Ate Five and Paramount Coffee Project.

Butter is an unexpected hybrid of fried chicken restaurant, sneaker store and Champagne bar, while Nomad is all about Mediterranean fare to share. At the higher end of the culinary spectrum is Toko, serving award-winning Japanese, and Longrain, famed for its impeccable South-East Asian cuisine. Don’t miss a visit to lively Chin Chin, the second installment of the famed Melbourne institution located in the renovated historic Griffiths Tea building, and walk-in wine bar Poly located just across the road. Enjoy the afternoon with a relaxing brew in The Beresford's outdoor beer garden, or at the ecclectic Dolphin Hotel.

Finish your adventure with a show at the Belvoir, one of Australia's most celebrated theatre companies. Many of Australia's most famous actors have performed here, including Geoffrey Rush, Cate Blanchett, Judy Davis and David Wenham. Alternatively, see a cult classic or a new release film at the historic Golden Age Cinema and Bar.

Potts Point

Largely occupied by Sydney's well heeled (and well fed), Potts Point is something of an inner-city oasis with a Parisian twist. With spectacular harbour views and leafy streets, this historic neighbourhood, just east of the city centre, is also characterised by a buzzing cafe culture and designer lapdogs out for their daily stroll. You needn't stroll far along Potts Point's leafy streets to notice the abundance of gorgeous Art Deco architecture dating back to the 1920s, as well as mansions from the 19th century. If you happen to be passing through one of the interconnecting laneways, you may notice a queue wrapped around one inconspicuous blue doorway. This tiny hole-in-the-wall is Room 10, and it serves some of the best coffee out of Potts Point, plus all-day breakfast and lunch that is definitely worth the wait.

Of all the elaborate homes and striking apartment blocks, one of the most celebrated landmarks is Elizabeth Bay House. Built in the 1830s on a hill commanding enviable views over Sydney Harbour, it is one of the most famous private houses ever built in Australia. Macleay Street, the main vein of Potts Point, is thick with shiny stores and boutiques like Becker Minty, a local favourite. It's a lifestyle concept store that unites home furnishings, art, men's and women's fashion, jewellery and perfume. For something already loved, Potts Point Vintage specialises in furs, wedding dresses and menswear, as well as English fine china.

With more than 200 restaurants within the Potts Point vicinity, food aficionados are spoilt for choice when it comes to dining out. Among the better-known landmarks is Fratelli Paradiso, which serves casual Italian fare, or for a decidedly more night-time setting, Monopole is a bar and restaurant in one, with expert cocktails and hearty, European-inspired share plates. Ms G's is another popular haunt, famed for its eclectic design and creative Asian menu.

Potts Point also has a flourishing creative community, providing a bevy of artistic entertainment for locals and visitors alike. For small-scale musical theatre or an intimate cabaret show, visit Hayes Theatre Co on Greenknowe Avenue, SBW Stables Theatre, or the Kings Cross Theatre (KXT), an indie theatre housed within the Kings Cross Hotel.

Marrickville

Marrickville, a multicultural suburb in Sydney's Inner West, is a great mix of a heaving high street, artisan producers, warehouse converted breweries, and some of the best places for brunch in the city.

Just 20 minutes southwest from the centre of Sydney, you can find Coffee Alchemy, a Marrickville favourite and regular on “Sydney's best coffee” lists. Try a latte made with the house standard Goodness Galileo blend or get a bit more creative with specialty roasts such as the Hairy Chest or Holy Hildegard. If it’s a meal you want, the Cornersmith is a must, with cool minimalist design and a regularly changing blackboard menu, the team sources its ingredients as freshly and ethically as possible. For a taste of Marrickville’s Vietnamese community, look out for the red awning on Illawarra road for what are widely considered the best banh mi (Vietnamese pork rolls) in Sydney. Huge queues form at Marrickville Pork Roll for its baked-on-the-premises baguette with rich strips of barbecued pork accompanied by fresh, crunchy vegetables and a house-made secret sauce.

Boutique beer lovers similarly huddle among the huge silver tanks of Batch Brewing Co in a converted warehouse away from the Marrickville town centre. American owners Andrew Fineran and Chris Sidwa started Batch with a pale ale from their home country but now have a huge range of specialty local brews. In the adjoining blocks you’ll find a number of similarly cool boutique brewery/bars to explore, like The Grifter, Stockade, Wildflower, and Poor Toms for gin fans.

On the weekend, the Addison Road Community Centre is home to the Marrickville Market, which showcases the area's organic producers and has stalls selling vintage goods and street food snacks. Nearby is the permanent warehouse of Reverse Garbage, a not-for-profit creative reuse centre that turns trash into treasure. Finish your adventure with a late-night visit to LazyBones Lounge, a local live jazz lounge that’s been a hit with locals since it opened in 2013.

Glebe

Nestled between two universities, this inner-city village, just five minutes from Sydney’s Central Station via bus or car, is home to an eclectic community of students, academics, activists and new-agers. You'll hear them discussing everything from chakras to Che Guevara in its casual eateries, bookstores and pocket-sized bars.

Glebe’s wake-up call is at The Wedge Espresso, which serves coffee using a variety of methods, such as filter and cold brew, alongside an all-day breakfast menu catering to the vegan and gluten free. Don't miss Glebe’s popular Saturday markets (10am to 4pm), where bargain hunters and bohemians flock for second-hand clothing, handmade arts and crafts and up-and-coming designers. There's a handful of food stalls selling everything from Turkish pide to artisan pastries for you to enjoy while listening to the soothing sounds of street performers on the lawn.

Bibliophiles head to Glebe for its string of local bookshops. Drop into independently run Gleebooks, where shelves are lined with the newest titles in Australian literature as well as crime, history and philosophy. Around the corner on Derwent Street, Florilegium specialises in gardening titles, with more than 5000 new and second-hand books. Sappho is another well-known book and record store, with a beautiful courtyard café that doubles as a wine bar in the evening.

Away from the hubbub of Glebe Point Road, there's peace and quiet to be found along the harbour foreshore. Glebe's waterfront encompasses four parks – Federal, Jubilee, Bicentennial and Blackwattle Bay – spanning more than 17 hectares (42 acres) of open grasslands, sports fields, playgrounds and wetlands. 

Cockatoo Island

Here’s something most visitors don’t realise: the best views in Sydney aren’t found in any of its five-star hotels. To wake up to the ultimate knock-your-socks-off views, check into one of Cockatoo Island's various accommodation options, from camping and glamping to apartments.

A short ferry ride from Sydney’s city centre, Cockatoo Island hosts exciting yearly events like the famous Biennale Sydney art festival. Don’t rush to leave in the morning because there is plenty to explore on Sydney Harbour’s largest island, including the sandstone convict barracks and the massive turbine hall, a relic of the island’s days as a shipbuilding base. Regular ferries run from Circular Quay.