Darling Harbour, Sydney, Australia

A Self Guided Stroll Around Sydney

A self guided stroll around Sydney is something you should do the first day you arrive – and by around, we mean around the city’s perimeter. The city of Sydney may look large with its lofty towers and mini Manhattan-like skyline, but Sydney’s city centre or CBD is surprisingly compact.

It’s Sydney’s metropolitan area that is massive, 4,000 square kilometres in size, making it one of the biggest cities in the world in terms of area, equal to that of London and nearly double New York City, sprawling in all directions to the mountains, plains, rivers, and sea.

Drive the 90 minutes from the city centre or CBD (that’s Central Business District, as we Australians like to call our downtowns) to the Blue Mountains and you’ll feel its immensity – especially when stuck in bumper-to-bumper traffic on Parramatta Road. You’re better off taking the train.

Yet the city centre, on the other hand, is compact enough for a self guided stroll around Sydney. The CBD is a manageable size. You can easily walk the diameter of the CBD as its widest point from Macquarie Street to Lime Street, a paltry 1.1kms, in 15 minutes, and do its length from Circular Quay to Central Station, just 2.7kms, in 35 minutes.

From Kings Cross, you can wander down to Darling Harbour, a similar distance, in the same amount of time. If you’re staying in Darlinghurst or The Cross, skip the underground and enjoy the fresh air.

Smooth wide footpaths, traffic lights most intersections, plenty of pedestrian-only zones in the forms of thoroughfares, parks, gardens, and plazas, and even-tempered locals (unlike, say, New York City; if you walk slower than Sydneysiders, they don’t get cranky) all make Sydney a very pleasant place to stroll.

Yet despite its small size and straightforward grid plan, Sydney is a city that visitors seem to easily get lost in, even with maps in their hands – I can’t tell you how many tourists I used to help each day in all the years I worked in the CBD. Sydney is also a city that visitors often seem at a loss as to how to negotiate and navigate, how to get their bearings, and where to start to explore, and I’m not sure why.

So this is what we recommend you do, before anything else: grab a map or use your iPhone and set aside a day simply to do a self guided stroll around Sydney.

If you start in the morning, take your time, make some detours along the way, and stop for lunch, you should finish in the late afternoon.

Our Self Guided Stroll Around Sydney

  1. From busy Circular Quay, where the ferries depart for various parts of Sydney Harbour, head toward Sydney Opera House, passing locals soaking up the sun at the cafés and bars, such as The Opera Bar, beneath the stunning edifice. Join them for a coffee to kickstart your stroll.

  2. Enter the Royal Botanic Gardens and walk along the waterfront path skirting Farm Cove, all the way to Mrs Macquarie’s Chair, around the peninsula, then hike up the hill by the harbourside Andrew (Boy) Charlton pool. Stop to admire the graceful old grey Woolloomooloo Finger Wharf, home to BLUE hotel and Otto Ristorante, one of Sydney’s best spots for lunch in the sun. Make a note to return.

  3. Push on up the hill and cross the bridge over the Cahill Expressway where you’ll see the imposing, sandstone Art Gallery of NSW. The permanent exhibition is free and the art museum is home to an impressive collection of Australian art, so pop in for a look.

  4. Cross the road and walk across the grassy Domain up to Shakespeare Place to the equally grand State Library of NSW. Pop in here for a peak too.

  5. Take a left and turn the corner and you’re on historic Macquarie Street, lined with handsome heritage buildings (on your left) that are some of Sydney’s oldest, including grand old Parliament House (where I once worked; dating to 1816, it was first part of the Rum Hospital), the majestic Sydney Hospital (dating to 1811), the elegant Sydney Mint (finished in 1816), and the stately Hyde Park Barracks, designed by convict architect, Francis Greenaway, Australia’s first notable architect who built many of Sydney’s most significant buildings.

  6. Cross the road and wander through lovely, leafy Hyde Park, Australia’s oldest public park, dating to 1878. Dip into St Mary’s Cathedral on the north side if church architecture interests you, otherwise, wander around the Archibald Fountain, and walk along the promenade shaded by enormous fig trees that is often used as a public outdoor gallery for art works, photography and installations. Cross Park Street, which splits the park in two, and continue to the poplar-lined pond, the Pool of Remembrance/Lake of Reflections, in front of the ANZAC War Memorial.

  7. Continue down Elizabeth Street, which borders the old garment district of Surry Hills on your left, to Belmont Park, in front of Central Station, and turn right into Hay Street and walk for a few blocks until you reach Paddy’s Market and Chinatown, perhaps the most animated and authentic Chinatown outside of Asia. If you’re hungry by now and you’re on budget lunch here (see this post for ideas), otherwise, turn right into Harbour Street in the direction of Darling Harbour.

  8. From here it’s a very pleasant stroll through Darling Harbour’s parks and gardens, along fountain promenades. First you’ll pass the Chinese Garden of Friendship, then the lawns of Tumbalong Park, where a lot of festivals and concerts are held. Once at the waterfront of Cockle Bay, which gets lively on weekends, stick to the left or western-side of the water, for the best views of the city skyline.

  9. Stroll by the white post-modern Harbourside complex (do not stop and eat here), past the Australian National Maritime Museum, in the direction of the reinvigorated neighbourhood of Pyrmont and The Star, a swish entertainment complex with casino, hotels (The Darling), apartments, theatres, shops, bars, and restaurants. Refuel here at a table with city and Harbour Bridge vistas at the Aussie take on a stylish Milanese osteria that is chef Stefano Manfredi’s superb restaurant BALLA.

  10. If energized, you could cross the road and walk down the end of the wharf to Ballarat Park and continue to explore the revitalized wharf district of Pyrmont, or, if feeling a little lazy after lunch, backtrack to Darling Harbour and cross Pyrmont Bridge over Cockle Bay and hike up one block to Kent Street.

  11. Turn left onto Kent Street and walk all the way along this street until you reach one of the CBDs most charming and oldest areas, The Rocks, which starts soon after High Street when you come to a row of quaint old workers’ cottages.

  12. Once you see the lovely old sandstone Lord Nelson’s Brewery, call in for a cold beer, before continuing down the hill to Hickson Road. Make a note where you are: we strongly recommend returning to this neck of the ’hood and exploring more. If you turn right at the pub onto Argyle Street, you’ll see Sydney Observatory, from where you have lovely views of the Bridge.

  13. Hickson Road is essentially Sydney’s theatre district with the superb Sydney Theatre Company, Sydney Dance Company, Bangarra Dance Theatre, and the Australian Theatre for Young People all located here in renovated old wharf complexes, as well as a marina, shops, cafés, and restaurants.

  14. Continue your amble until the end of the point – there are stunning views to the West from a small wharf, which are wonderful at sunset – then stroll under the Sydney Harbour Bridge to Dawes Point Reserve for spectacular views of the Sydney Opera House.

  15. Stroll around the waterfront, in front of the recently reopened Park Hyatt Sydney and Sydney Cruise Ship Terminal for more stupendous views, passing the Museum of Contemporary Art (worth a look, and it also boasts a restaurant/bar) and First Fleet Park, until you reach your starting point, Circular Quay.

By now you’re probably exhausted after your self-guided stroll around Sydney, your feet are killing you, and you’re cursing us. Don’t worry, in true Aussie-style, everything will be fixed with a drink.

Stagger around to the Opera Bar, which you passed this morning, order a glass of wine, and watch the sunset. Weather not on your side? Head across to The Rocks for an icy beer at an old pub.

Get out that map again and mark up all the places that intrigued you. You can revisit them in coming days…



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