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Track difficulty: Medium
Terrain elevation: Flat and inclined
Estimated time: 1 hour (non-stop). 2 hours(stopping for pictures)
Steps: 5000 approx
Need: Yoga mat to do your morning stretch in front of the Harbour Bridge
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Considered one of the most established and affluent suburbs in Sydney, Kirribilli is synonym of water views, gorgeous lookouts, and the 'other face' of where the Sydney Harbour Bridge can be looked from. It is also the location of one of the two official residences of Australia's Prime Minister. But most importantly the favourite spot of Winson, our CitiTrails local of today.

Milsons Park
Winson is into Jiu-Jitsu, and the reason he likes to come to Kirribilli is because he likes a space in the city with plenty of spaces to walk, meditate, and take a break from the city noise.

Water views can be seen from everywhere in Milsons Park. However, the park itself has a nice recreation area and has a beauty on its own.

Walking down around this area is very peaceful. It helps me forget about my worries for a bit. It is also very convenient as you pretty much have lots of transport options. Besides, you've got everything! here Cafe, shops, and convenience stores are always couple of minutes away.
Winson recommends coming to this same exact place around Spring (Sep - Nov). No longer need to longer guess why...


Must definitely The Flying Bear Cafe has one of the best views of this area. It is highly recommended that you have a coffee here and enjoy the tranquil atmosphere of parked boats in front of you.


Kirribilli House
A couple of blocks away, Winson recommends to have a visit to the Kirribilli House - the second official house of the Australian Primer Minister. This area is of high importance as next to it you can also find the Admiral House - the accommodation premises that served to King Charles III in his later visit to Australia on October 2024.
It is unfortunate however, that you are not allowed in. So we just decided to show Winson very casually outside of the Kirribilli House entrance.

The Lady Gowrie Lookout can definitely replace the view that you may be missing from not being allowed into the Kirribilli House. In fact, is just walking down the same street.
Yacht views are not bad while I like to walk around and do some casual stretches that keep me going. I believe I'm very lucky to come to this lovely suburb. You get the most beautiful views you can ever imagine.


Dr. Mary Booth Lookout & Under the Bridge
Make sure to head down to Dr. Mary Booth Lookout via Beulah St. This will give you the Opera view you never imagined and its CitiTrails endorsed.
I like Jiu-Jitsu because its a philosophy I apply to my daily life. This has helped me a lot to teach others what I do. Coding is one of my passions and I like teaching people to learn how to code. But I also like good artwork and I like to stamp my Jiu-Jitsu shirts with some of it.


Having arrived to Dr. Mary Booth Lookout, you get to appreciate the other side of Sydney that you are most used to see from the Opera House. This time the residential houses are at the back and its time to take a sit and relax.


I have moved many places in my life. And I regret nothing on choosing Sydney as my actual place. I have everything here and I make sure to enjoy every second of it. Even though you can see we had bit of a grey day, the scenery remains beautiful as it is. I definitely advise people to come here to spend a couple of hours.

If you keep walking towards the bridge along the shore, you will find many other people doing picnics, relaxing, fishing, or even professional photographers with big cameras ready to take the shot of their lives.


Luna Park & Wendy Whiteley's Garden
After you pass the Harbour bridge (under it) if you keep walking along the shore this will take you to the entrance of one of the most emblematic places of Sydney: Luna Park. A heritage-listed amusement park operating since 1935.

Although we did not decide to make this trail a dedicated one to Luna Park, Winson advises visitors to at least jump into the wheel to take some extra pictures of the Sydney Harbour.
Also: It is very cool to get into some of the rides.


Back on the trail. There is a picnic area if you keep walking alongside Luna Park. Here, you can take more pictures noticing how the landscape changes and you get a further shot of the Harbour while coming closer to the North Sydney area.

I'd like to finish our trail heading up to the Garden's (Wendy Whiteley's Garden). This is another secluded space that is rarely found in the City. A place where there are multiple plants, bird species and flowers that I like. Many people working around North Sydney are too busy to walk around these paths. Feels like two parallel worlds you can see at a time.


CitiTrails Challenge: Can you figure out exactly where is this spot located at Wendy Whiteley's Garden? If you can take a similar picture like the one below, we are offering a 15% discount on your next meal at the bonus location point.

Bonus: Lavendra Indian
Details here
Winson's favourite way to end the day: At a refined Indian Cuisine restaurant with views towards the Sydney Harbour and excellent hospitality. This is a most if you were to impress your friends, family or partner as every dish here is an experience.
Biryani rice, butter chicken, and garlic & cheese naan were some of the dishes ordered on the night. Look at the beauty of them.




The Murgh Makhani was definitely the winner this time.
Winson Tan is currently working on helping others to learn how to code, with Code Dojo Au. Based on thr Jiu-Jitsu philosophy 'The Art of Practising', Winson tries to replicate this centennial mixed martial art principle into many of his workshops that run every 2-3 weeks in the City. Come check it out.
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