The best way to explore any city is by walking it. The same applies to Sydney. By living in the area of Darlinghurst, as we recommend, you have the perfect base for your on-foot exploration.
In this itinerary, I suggest two different walking tours, as a general guide and idea. Please explore for yourself apart from these suggested itineraries. 😇
The Tourist Tour: Stroll through the Royal Botanic Gardens to the Opera House, Harbour Bridge, and The Rocks
The Local Tour: Discover local neighborhoods such as Darlinghurst, Kings Cross, Paddington, and Darling Harbour
The Tourist Tour
We got to be honest, even if we don't like to be called tourist, heading to these famous sights makes us such - even if just for a moment. More importantly, your visit to Sydney would not be complete without a visit to the Opera House and its surrounding area. So put on your walking shoes and take the scenic walking tour through the Royal Botanic Garden and learn about the local flora. Enjoy the peacefulness of the park and head closer to the Opera House.
For me, it was a magical moment laying my eyes for the first time on this inspiring structure. Let's see how you will feel 😊.
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Take your time at the Opera House to really take in the construction and head for a drink at the Opera Bar. It is usually super crowded as it offers amazing views. Only on Easter Friday (one of two days in the year), it is empty and soulless. Such a unique picture without any people in it.
Keep heading along Circular Quay, Sydney's biggest harbor, and continue towards the Harbour Bridge. If you haven't had a bite yet and feel a sense of appetite, The Squire's Landing is an excellent location for dinner and drinks with views of the Opera House and the Harbour Bridge.
Afterward, keep heading up to the historic The Rocks neighborhood with its laneways full of galleries and pubs. Some of them being the oldest pubs in all of Sydney. If you are a sucker for live music, like we are, this will be heaven to you 😆. So be sure to stick around for the evening.
Two pubs we can recommend, and we spent quite some time at are the Mercantile Hotel and the Fortune of War both on George Street. The latter being arguably the oldest pub in the city.
This entire walk is about 5-6 km / 3.1-3.7 miles and will take a bit over an hour purely walking. With all the stops along the way, estimate a minimum of 3 hours plus your dinner and drinks time.
The Local Tour
It is time to step away from the many waterfronts for some time, to discover different in and cool neighborhoods. Start around the area you are living, such as Darlinghurst, head to Kings Cross during the day to discover some lifestyle cafes and quieter streets than at night. Kings Cross is the red light area of Sydney and therefore spices up after the sun sets.
Next head towards Paddington, an upscale area with Victorian terraced buildings and lively shops and cafes. Walk by the Paddington Fiveways, a cool intersection of five roads with cute cafes on the corners. On a Saturday head all the way down to the Paddington Market, where you will find stalls selling trendy clothes and crafts.
Its time to turn around and follow Oxford Street all the way back up towards the CBD. You will see its cafes and atmosphere change every few hundred meters. Take a stop at Hyde Park, Sydney's oldest park grounds. Keep heading straight towards Tumbalong Park and maybe make a stop at the Chinese Garden of Friendship.
Next up, you have reached the end of this walking tour arriving at Darling Harbour, a big pedestrian-only recreational area along the waterfront. You will find an uncountable amount of shops, restaurants, bars and modern high rises reflecting in the water.
Should you be there on a Saturday, grab a table overlooking the waterfront for cool fireworks at 9 pm. Should you be interested in Maritime History, keep heading for the big white Cape Bowling Green Lighthouse. You have reached the Australian Maritime Museum with a submarine and sailboats on display in the harbor.
Walk over the pedestrian-only Pyrmont Bridge and grab an Uber to call it a day.
This walking tour is about 8 km / 5 miles long and will take you a little under two hours of pure walking. Again plan at least 3 hours, we recommend to do it during the late afternoon and evening for an in-depth experience.
Add on to the Local Tour: Strap on your running shoes one morning and go for a sunrise run along the waterfront of Rushcutters Bay and Darling Point. I wish we would have those views and atmosphere at home in Germany 😅.
