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 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. 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.

Historic streets of Sydney  © Mark Bowyer 2021© 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 Saturdays and Sundays and other days for special bookings. Put your own group together (min. 5) and let us know. 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 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 1.30PM and concludes at 5.00PM (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.


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.


Book Tour