Sydney - Tales of the City

Sydney – Tales of the City is a unique walk through Sydney’s past. It’s an experience of history, architecture and the energy of Australia’s oldest and largest city. We’ll get a sense of the cruelty and dispossession of the colonial invasion of 1788, and the messy, improbable journey that transformed Sydney from a violent penal colony into one of the world’s most liveable, prosperous, diverse and envied modern cities.

We’ll admire the splendour of the city’s built environment – and we’ll note the eras of development over two centuries. We’ll visit the Botanical Gardens and the famed harbour that flatters everything around it. We’ll dig into the stories and meet the characters behind the buildings, and the bungles, and we’ll explore and explode some of the myths.

Hyde Park Convict Barracks, Sydney

Hyde Park Convict Barracks, Sydney
© Mark Bowyer

Sydney – Tales of the City is a sweeping survey of the good and the not so good, in stunning Sydney surrounds, that will leave you with memorable insights into the city and its people. The feel is informal and informative. It’s designed for people who like to dig a little deeper – whether you’re a visitor or a local.

We time our walk each day for optimum light (perfect for photographers) and we finish for the end of the day by the harbour and the Opera House.

Highlights of our walk include Hyde Park Barracks and St James Church, the Royal Botanical Gardens, the architectural evolution of the city, Macquarie St, the Opera House and Harbour Bridge.

The fine figs of the Royal Botanical Gardens                                                                                                                © Mark Bowyer


The tour operates Thursdays, Fridays, Saturdays and Sundays from February 4 2021. Send us a booking or email us.


$85 per person including one drink.  Tours operate with a minimum 2 people. If we don’t have two travellers, the cost for a single (private tour) will be $160. For scheduled private tours, see below.


Expert guide, drinks, presentation. Small group (max 8) experience.


There are no entrance fees.


You’re a curious, active traveller interested in exploring the stories of Sydney – past and present – on foot. You’ll need to be mobile – but we move at a casual speed. Expect to be on your feet for 3 – 4 hours with some breaks. Sydney can be hot in summer. We begin our tour as the afternoon begins to cool and most of the tour is conducted along shaded paths. We operate in all weather conditions. The feel is informal and informative. The tour is designed for people who like to dig a little deeper. You may have some prior knowledge – whether you’re a visitor or a Sydney local. The tour is an excellent introduction to all things Sydney.


The tour commences at 3.30PM and concludes at 7.00PM. We finish with a drink and a chat overlooking Sydney Harbour. It’s a great way to round off our Sydney experience and to discuss some of the issues that have come up during the tour.

NB. Tour operating hours vary depending on the seasons and daylight saving times. In winter we begin at 2PM. We’ll let you know when you book.


Comfortable walking shoes, hat, sunscreen, water bottle.


You can put your own tour together and we can talk about your special interests. Special discounts apply to private tours of more than 5.


We acknowledge the traditional custodians of the Country on which we walk on this tour, the Gadigal of the Eora Nation, and recognise their continuing connection to land, waters and culture.

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