Aussie’s love their great outdoors; the warm clear sunshine, the sand, surf and sea of the bounteous coastline that uniquely rubs shoulders with one of the worlds most cosmopolitan cities. Though the centre of Sydney is a thriving financial CBD, the real heart of the city is its expansive blue Harbour. It was because of its Harbour the colony of Sydney was first settled and why today Sydney is considered one of the world’s prettiest and most welcoming cities. Our insider’s guide takes you through the backstreets, around the bays and across the bridges of this truly unique holiday escape.

Room with a view

The waterways of the Harbour that stretch from Sydney’s suburban edge out the Heads sparkle as they blend with the city. Few places will give you a clearer vista than the pinnacle of the Harbour Bridge. It takes a good couple of hours to do the 1,332 Bridgeclimb but throughout the journey, you’re as enthralled with the stories of survival and triumph as much as the stunning outlook. Peering across to the milky white Opera House is spectacular, but the most alluring way to see the iconic shells is to walk from The Rocks winding through Circular Quay past the Ferry Terminal up to the grand staircase. There are plenty of fine dining options but it’s the lookout and providential food philosophy of Bennelong Restaurant that makes it a favourite. On the rooftop of Customs House, Cafe Sydney with its cocktail lounge and modern Australian menu also offers one of the most pristine aspects of the harbour.

Experiencing Sydney at street level gives you a feel for its character. The I’m Free walking tour starts at Town Hall Square and meanders through the backstreets bringing to life Sydney’s famous landmarks and infamous convict characters and of course, the quirky hole-in-the-wall coffee spots. Yes, Sydney-siders like their coffee. From the east of Sydney, It’s a stunning coastal drive from the city down New South Head Road, through Vaucluse and down to Watson’s Bay. It only takes about half an hour to reach, but the dazzling views along the shoreline of Macquarie Lighthouse and North Head make it easy to lose track of time. The azure expanse of sea is visible through the homes perched atop the undulating streets and every now and again as you wind downhill, the city skyline appears. At Watson’s Bay, the boardwalk spills over the sand as paddle boarders skim the gentle waters. There are colourful umbrella’s, ice creameries and some of Sydney’s favourite restaurants lining the walkway and every day looks like summer.

City of villages

Connected across the spread of Sydney are the stylish little hubs of Sydney known for their cool cafe’s, eclectic homewares and designer boutiques. Straight up Sydney’s main George Street, near Central Station bordering Chinatown, you’ll reach the innermost suburb of Ultimo. It’s a haven for students with two Unis and a number of colleges nearby. Shopping is fun and the food (with a fusion Asian influence) is cheap and cheerful. Ultimo is also around the corner from Newtown’s King Street. As well as great clubs, pubs and eateries King Street is packed with one-off designers, op shops and jewellery stores all with a retro influence.

A little more upscale and home to some of the countries most swish designers are Paddington (the northern end of Oxford Street) and Balmain (just across the Glebe Island Bridge). Both suburbs are characterized by their dappled leafy streets, Victorian terraces and modern cafes and are home to Saturday outdoor markets, peddling original art pieces, local craft and freshly grown local produce. Another favourite is Surry Hills, a little pocket of corner cafes and handmade designer ware wedged between Central and Redfern. As the circle of inner Sydney, these fringe suburbs are easy to reach by bus or foot and make for a day of happy discovery.

Beyond Bondi

It’s hard to miss a trip to Sydney’s most recognizable Bondi Beach and the coastal walk to Bronte. For a first-timer, the walk over the waving cliff edges and taking in the stretch of the Pacific Ocean is spectacular. But beyond Sydney’s most favourite tourist beach is a coastline that offers some of her less travelled and best hideaway beaches. And though Bronte isn’t actually secluded, it makes our list of recommended beach breaks. That’s because the little nape of road that leads you to the beach and Bronte Park is lined with gorgeous little cafes with their little mismatched tables and big breakfast options.

At the most northern peninsula of Sydney’s coast stands Barrenjoey Lighthouse and Palm Beach. It’s an open wild sea and the winding hilly drive gives way to spectacular views of an exposed line of beaches from Narrabeen to Whale Beach, as famous for the wryly named Jonah’s restaurant and guesthouse. A little closer to the city is the lesser frequented Nielsen Beach, which like Bronte backs onto beautiful grassy parklands. The beach is small, the cafe is sweet and is just around the corner from Parsley Bay, another of the cities more reclusive beaches. But if it’s the beautiful people and stylish beachside eateries you’re looking for, Balmoral Beach on Sydney’s lower north shore really sums up the best of upmarket summertime.

Bondi Icebergs

Art and Culture

Between Sydney and Melbourne, there’s an old rivalry to bring art and culture alive. And though it may come more naturally to the Victorian capital, Sydney’s art scene is evolving quickly. Today, with it’s blossoming cultural niche, Sydney hosts dozens of festivals each year, and it’s namesake The Sydney Festival happens each January. It’s a creative collection of music, movement, theatre, arts and entertainment that has been the hallmark of a Sydney summer for 40 years. The festival exhibitions are dotted all over the city which suits Sydney well, it means people can walk casually around in denim shorts, flip-flops and splashes of sunscreen from one outdoor venue to another. Because of the holiday feel of summer and Australian’s love of the great outdoors, there are pockets of art and culture popping up everywhere. Along the foreshore of Circular Quay The Museum of Contemporary Art is a burgeoning of talent and from the other side of the Quay, the Australian Museum and National Art Gallery are just a short stroll away. Sydney is a city of expressionism so keep an eye on The Opera House theatre and dance program, The Enmore Theatre event guide and the Gig Guide.

Day trips from Sydney

For all of Sydney’s corners to check out, it’s by taking a short drive out of the city that you’ll get a feel for the rolling countryside that hugs the coastline making Sydney so unique. Just 2 hours drive west and you’ll reach the hazy skyline of the mountains. What makes the Blue Mountains so special are the connection of little villages that spill over the countryside and the foliage of a cooler climate that makes it so different from Sydney’s beachside feel. Head south and the inland farms and heritage townships of Berrima and Bowral are a real escape to the country. Quaint cafes, fireside lounges and stores loaded with handmade delicacies fill the laneways.

If you choose to drive up the north coast, the spread of beachside towns continues. Port Stephens is a wonderful summer getaway for dolphin watching, water sports and camping where you can watch the sun rise over one beach and watch it set over another. A favourite way to enjoy a weekend escape is to spend a day in Port Stephens and then continue inland to the Hunter Valley, Sydney’s wine country. With over 150 wineries to while away the afternoon in, keep a watch on upcoming events too at the Hunter Valley Visitor Centre. As well as local organic treats, delicious cheeses and handpicked wines, the Hunter is a hub of cultural entertainment and a perfect cosy winter escape for two.