Sydney - Tales of the City

Sydney – Tales of the City is a unique walk through Sydney’s past. It’s an experience of the history, the characters and the energy of Australia’s oldest and largest city, in a casual, small-group setting. 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 miserable, violent penal colony into one of the world’s most liveable, prosperous, diverse and envied modern cities. There’s plenty of time for chat and questions.

We’ll admire the splendour of Sydney’s built environment – and we’ll note blunders in the eras of development over two centuries. We’ll visit the Botanical Gardens and the famed harbour. 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.

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. It’s a perfect introduction to the city and its past. 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 and the Royal Botanical Gardens. We finish by the Harbour looking over the Opera House and the Sydney Harbour Bridge.

Even if you’re from Sydney, you’re bound to see and hear new things.

In a place remembering colonial wars, the war of survival waged by First Nations is incomprehensible. © Mark Bowyer                          

Sydney – Tales of the City is led by our founder Mark Bowyer. Mark was born and raised in Sydney’s Western Suburbs. He studied Australian history at Sydney University and the University of Technology before working in media and tourism. He publishes the travel guide.

Mark says,”Returning to Sydney after decades abroad has given me an opportunity to take a fresh look at the place and its incredible, complicated past. The way we view history has changed too. That’s good. I’ve learned a lot. I’ve created a tour here that tells Sydney’s chequered story, while showcasing its stunning, photogenic, beauty.”


The tour operates on Sundays and other days for special bookings (contact us at Put your own group together (min. 5). Send a booking using the form or email us.


$65 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 $120. For private tours, see below.


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


There are no entrance fees.


You’re a curious, active traveller (over 12 years of age) 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 1.00PM and concludes at 4.30PM (winter). 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 history and ideas that have come up during the tour.

NB. Tour operating hours vary depending on the seasons and daylight saving times. The tour is timed to experience the city in the best afternoon light.


Comfortable walking shoes, hat, sunscreen, water bottle and warmth in winter.


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.


The tour is available to anyone over 12 years of age with average fitness and mobility (ask us about family walks an walks for the less mobile). We walk around 9000 steps over 3.5 hours on mostly flat terrain. There are some steps. Families with younger children can organise a private tour.

We operate in all but the most wild weather conditions. If we cancel due to weather or another externality, we will provide an alternate tour date or a full refund. Otherwise, one date change can be made up to 12 hours prior to the tour without penalty. There are no refunds for cancellations.


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