If you have read my article MBA in Australia after 45, you probably already know that I have been discovering Sydney and its surroundings like crazy since I arrived. I spent every weekend in a different location, visiting new lookouts, exploring new trails through the bushes or along the coastline. As a traveller, I usually look for sites with energy, the spots with peculiarities, in other words, places with a special aura, where you can completely immerse yourself into the atmosphere and deeply feel this place rather than just look at it.
With this approach, I have compiled a list of my favourite Sydney trails, which includes both famous and lesser-known Sydney attractions, but they all have a unique vibe, at least that’s how I feel them.
#1 route: Wendy’s Secret Garden – Kirribilli – Harbour Bridge – The Rocks
I’ll start with my favourite route. When guests from abroad come to Sydney, and I play the role of a guide, I usually begin with this particular route. Because this route allows you to start exploring the city as if from afar and without haste, gradually plunging into the bustle of the city. This is especially critical if you are after a long flight and don’t want to be overwhelmed by crowded places. On the other hand, this track provides the opportunity to see iconic landmarks such as the Opera House and the Harbor Bridge from distance and take some beautiful photos from a favourable vantage point.
To get to Wendy’s Secret Garden, I suggest taking the train to North Sydney station. Then walk down to Blues Point Road, turn left onto Lavender Street and, past Watt Park, reach your destination. The reason for this loop is simple. In this case, you can catch a bit of the North Sydney area, which is quite interesting to see. It is a mix of modern skyscrapers and charming gingerbread houses, expensive brand stores and small authentic shops and stalls, a vibrant business atmosphere, especially on weekdays, and tiny parks like Watt Park, which are relaxing mentioned earlier. So, don’t deprive yourself of this pleasure and walk around the area.
I was lucky enough to meet Wendy Whiteley, the creator of this lovely garden, in one of the events that Art Gallery society throws for members. She talked about her husband, the famous Australian artist Brett Whiteley, and how, after his death, to distract herself from grief, she started to clean the dirty area near her house. After finishing the clearing, she began to create a garden in the form of a giant painting. Step by step, it turned into a beautiful garden, which still delights visitors who accidentally wandered here, apparently to enjoy the coolness created by the foliage of gigantic trees and the scent of flowering shrubs. More stories about this amazing place can be found here.
If you are travelling with children, be sure to visit Luna Park, which is nearby. You can take a ride on the Ferris Wheel or Rollercoaster and have fun with all that cotton candy or fairy floss, whatever you call it, stuff. Otherwise, you can cross over to the other side of the railroad via Milsons Point station and walk through the Kirribilli area to reach the Flying Bear Cafe, where you can spend time sipping wine, chatting and enjoying the view of the bay where the yachts sail slowly back and forth looking for their berths.
Travelling between October and November, it is impossible to miss ‘Jacaranda’s Paradise’ – the McDougall Street – which is located just next to the Flying Bear Café. This is the most popular street in Sydney for photographing with Jacaranda in the background, much to the regret of residents. During these months, this street is crowded with onlookers, and because of it, it leads to quite large traffic jams. But this place is definitely worth a visit!
After resting and energising yourself, make a forced march across the Harbour Bridge. To do this, return to Milson Point Station and climb up to the Harbor Bridge. If you don’t pause for photos, it will take about a 20-minute walk to get to the other side of the bridge. However, I suggest stopping by the Harbour Bridge Pylon Lookout which is easy to find.
Oddly enough, it’s one of the most understated tourist attractions in Sydney. You would be surprised how many locals have never been to this lookout and a small museum with interesting details about the history behind the bridge, not to mention the breathtaking view from the top. So, it’s both enjoyable and educational for everyone. Check it out.
On the other side of the Harbour Bridge is The Rocks area – the best place to wrap up the long day. This domain got its name from members of the First Fleet, who landed on this rocky peninsula in 1788 (more history is here.
This is perhaps the most historic area in Sydney, where locals and tourists alike love to stroll through the Rocks Markets (https://www.therocks.com/), testing street food (including crocodile and kangaroo meat) and buying a variety of handicrafts. The area is also home to some of Sydney’s oldest pubs and an array of high-end restaurants overlooking the bay. In other words, landing in one of the coziest pubs or cafes, listening to the street musicians and reflecting on the past day might be the best way to end such a busy day.
#2 route: Martin Place – State Library – Art Gallery – Botanic Garden
My second favourite route in Sydney starts from Martin Place (near the train station of the same name). What I love about Martin Place is that you never know who you will meet there, from your ex-flatmate to a celebrity. This is the heart of Sydney, the place where all roads lead. It became a national Australian icon by bringing high-profile films and television programs and actors to the area. It is also home to a heritage-listed landmark building – the General Post Office – commonly known as the Sydney GPO. For more history of this wonderful place take a look here.
By the way, at Christmas, the main tree flaunts here as well.
Having seeing Martin Place, walk down Macquarie Street to the State Library of New South Wales. What I love about Aussie libraries, is their art and history collections inside. In my opinion, the exhibitions in libraries and some universities here are so amazing that sometimes they turn out to be more interesting and substantial than the collections of respectful national museums. In addition, the State Library of NSW is the oldest in Australia and, like all historic libraries, ‘dust flickers in the light here and silence fills your ears.’ But the first thing most people notice in all old libraries is the smell – the scent of old books that tingles the nose. The State Library of NSW is no exception and it’s mmm… unforgettable.
The Art Gallery of New South Wales is a 10-minute walk from the library. I like to drop in here from time to time to recharge my batteries and fill my inner artist with creativity. Here you can enjoy free permanent exhibitions of Australian and European artists. Or if you’re lucky, you might catch temporary exhibitions from one of the famous museums, such as the Hermitage or Stockholm Museum. In addition, the gallery has a quite dynamic public events program. Having come here to contemplate works of art, you might suddenly become a participant in a creative discussion or a listener to a live concert. Check out their website before going there.
Now it’s time to go to the Royal Botanic Garden. Established in 1816, it is the oldest botanical garden and scientific institution in Australia. Most of their plant collection comes from Australia and the South Pacific. However, specimens from all over the world can be found here too. Interestingly, although the garden doesn’t look huge, every time I go here (almost fortnightly) I stumble upon some area that I haven’t discovered before. I mean, make sure you have at least an hour or two to explore this beautiful place.
Once you make your way through the garden to the waterfront, you have a few options. One of them is to turn left and end the day at one of the cafes or restaurants of Circular Quay. Or, if it’s sunset time, I highly recommend wrapping up your day at Macquarie Point. To get there, just turn right near the embankment and keep walking until Mrs Macquarie’s Chair, you won’t miss it. This vantage point offers great views of the Harbor Bridge and the Opera House, especially at sunset!
#3 route: Barangaroo – Sydney Aquarium – China Garden – Darling Harbour
My third favourite route starts from Barangaroo. The best way to reach the area is to get off at Wynyard Station and follow the signs for Barangaroo. It is just a four-minute walk through the new tunnel, which is also a local landmark.
The Barangaroo site indicates Aboriginal occupation dating back some 6,000 years (more history about this amazing place is here. Nowadays it is the newest harbourside suburb in Sydney with waterfront restaurants, landscaped parkland, fascinating tour opportunities and a ferry wharf from which you can get Circular Quay or any other destination.
Once you arrived at the Barangaroo Wharf, turn to the left and you will come across a spot where you can enjoy Sea Life Aquarium, Wild Life Zoo and Sydney Madame Tussauds Museum at the same time. I can’t say I’m a fan of this place but if you wish to see the ‘Aussie Big 5’ (including Kangaroos, Koalas, Wombat, Platypus and giant Saltwater Crocodile), discover an amazing underwater world and take photos with some Hollywood stars, this place is exactly for you! For more information on this entertainment spot, check out their website before heading there.
There is no better place to unwind after such serious entertainment than the Chinese Garden of Friendship, which is just a 10-minute walk from the Aquarium. Outside, the garden looks rather modest, but once inside, you will surely be surprised by its beauty and serenity. It was developed by the Taoist principles of ‘Yin-Yang’ – the balance of opposing but complementary forces – and ‘Wu-Xing’ – the harmonious five elements: wood, fire, earth, metal and water. This harmony can be felt with all senses, literally.
Just take a walk along serene paths and admire exotic plants, blooming flowers and a lake of shimmering Koi. If you would like to stay for a while, check out The Gardens by Lotus, an on-site cultural heritage teahouse serving dumplings, Chinese tea and incendiary Sichuan cuisine. From time to time, I go here and enjoy this peace and tranquillity, it always brings me back to a harmonious state.
To wrap up the day, go back to the Darling Harbour area. There are plenty of cafes and restaurants with various cuisines for every taste; Tumbalong Park is a paradise for children; a Ferris Wheel from where a bird ‘s-eye view of the surroundings opens; and the Maritime Museum in case you feel you need more fun. What’s more, every season, the local business community and government host various festivals with different activities such as an open-air cinema, an ice-skating rink or a Lego Park, etc.
Finally, Darling Harbour is home to the city’s most iconic fireworks. So, every Saturday at 7.30 pm and 9 pm you can enjoy an incredible pyrotechnics display of multicoloured fireworks here. Day and time are subject to change, for more information visit this website.
#4 route: Sydney Uni – George Street – Angel Place – Circular Quay – Manly
This track is a mixture of cultural and slightly relaxing places. I suggest starting at the University of Sydney (USyd), which is located just outside the city centre, just a 5–10-minute walk from Redfern Station. Founded in 1850, it is Australia’s oldest university. In 2015, the British Daily Telegraph ranked USyd as one of the ten most beautiful universities in the world. I couldn’t agree more. For me, it looks more like Cambridge University and, by the way, produced many award winners too.
As I mentioned earlier, the exhibitions of some of Aussie’s universities are incredible, sometimes much better collections of respectful national museums and the USyd’s museum – Chau Chak Wing – is no exception. The entrance to the Museum is located on University Place, directly across from the Great Hall and Quadrangle lawns, and next to Fisher Library, you can’t miss it. It’s opened 7 days a week, but still, it is better to check opening hours before going there.
After such a cultural tour, it’s time to immerse yourself in the hustle and bustle of the city, strolling along with one of the busiest streets in the centre of Sydney – George Street. It was and still is the aorta of the city that connects a number of the most important buildings and precincts. There are more skyscrapers here than on any other street in Australia, with the highest concentration of offices of the largest public Aussie and International companies.
George street is usually overcrowded all over the week, but if you manage to go early in the morning on the weekend, there is a good chance of not getting stuck in the crowds. In this case, you will be able to observe and discover, if you wish, some of the historic buildings such as the Sydney Town Hall, St Andrew’s Cathedral, the Queen Victoria Building and other buildings in Victorian Regency style. Here is a link, where you can find a lot more information about almost every building, historical and modern, their architects, constructive styles, and even about the ghosts that live in some buildings.
As you walk down George Street, don’t miss one intriguing place called Angel Place. It’s easy to miss because it’s tucked away in a tiny alleyway between George and Pitt Streets. The place is famous for its public piece – Forgotten Songs, an installation of empty birdcages created by Michael Hill. The main idea of this work is to show how the fauna of Sydney has developed and adapted to coexistence with increasing urbanization. Moreover, it is one of the most popular destinations for photographers. It looks magically in both sunlight and lanterns.
Sailing like this along the seething stream of the city bustle, you will find yourself at the central hub of the city – the Circular Embankment. If you’ve already explored the second route on the list, you should be familiar with this area. The history of this place is connected with the history of indigenous peoples, which is worth knowing and which can be found here.
The Circular Quay is the centre of everything. It has not only a significant history but also a fascinating collection of surrounding landmarks with exceptional views of the Harbor Bridge, which languishes nearby. There is often a bustling life filled with vibrant scenes from both locals and tourists alike, especially when the sun is shining. A regularly changing ferry schedule leaves every few minutes connecting other parts of the harbour such as Watsons Bay, Taronga Zoo, etc., including Manly, where we are going to go.
It takes 15-30 minutes to get there from Circular Quay (it depends on the type of ferry: fast lane or the general public ferry). During the ferry journey, you will be able to enjoy the breathtaking views of the city of Sydney from the water. Besides, you can take the 1001st photo with the Opera House and Harbor Bridge in the background, which will be the pearl in your collection, for sure.
Actually, Manly is my Aussie favourite beach. It was the first place where I went after I moved to Sydney. It was definitely love at first sight. There is plenty to do there chilling on the coast, snorkelling on the Shelly beach (which is just a 20-minute walk along the Manly coastal line), browsing the Manly Art and Craft Market, or enjoying the ocean sitting in one of the local cafes.
Depending on what time of the day you arrive there, I recommend walking towards Shelly Beach to watch the sunset. Shelly Beach is located on the opposite side to Manly Wharf – the ocean side. When you get to the ocean, turn right and find a comfortable position to watch the clouds in the sky changing their colour during this incredible ‘sunset performance’. Otherwise, you can chill in one of the local bars or restaurants over there.
I am sure that you will never forget the atmosphere of these places that I have indicated. Having lived here for several years, I still visit these places from time to time, and no matter how many times I examine them, each time I find something new for myself and get real pleasure from it.
My list of “Aussie’s most atmospheric routes” is beyond the scope of the above. I have many more interesting places with stories. An additional must-see list in Sydney and Australia can be found here.
Finally, to make organising your tour easier, here are some useful links. The best and simplest way to find cheap flights to Sydney is Aviasales. For booking your accommodation, personally, I use whether Booking.com or Hotellook.com. To book tours and day trips, I highly recommend Viatorwith free cancellation and payment options to suit any plan or budget.
Otherwise, you always can ask me personally by sending an email. As someone familiar with Sydney, I would be happy to share with you my thoughts on where to stay, what to do and where to go here.
PS. This post may contain affiliate links.