Sydney - Tales of the City

Sydney – Tales of the City is a unique walk through Sydney’s past. With the intimacy and low-impact of a small group (maximum 8), we experience the history, architecture, art and energy of Australia’s oldest and largest city. Explore Sydney’s spectacular beauty, its gardens and harbour, as we examine the improbable journey, that transformed a violent penal colony, into one of the world’s most admired modern cities.  Our walks share big stories, beautiful scenes – with a sense of humour.

COST: $95per person including 10% GST and harbourside drink. Commences 2PM – ends around 4.30 – 5PM with option to stay longer for chat. Our walks inspire lots of interesting Sydney conversations (April – October)

Send us a booking or call us in Sydney on 0426638642

Sydney Tales of the City highlights –

Discover –
* The cruelty of the colonial invasion of 1788, and the messy, improbable journey that transformed Sydney from a starving, violent, convict colony, into one of the world’s most liveable, prosperous, diverse and envied modern cities.
* The natural and built splendour of the city from convict colony to the present.
* How the telling of Australia’s stories is changing.
* Australia’s continuing curious relationship with Britain.
* Sydney’s first major First Nations monument (from 2022) and its fascinating relationship with the harbour.
* The extraordinary characters and battles behind Sydney’s two greatest human creations – The Opera House and The Harbour Bridge.
* The dazzling photogenic beauty of the city.

Our personalised small-group approach means there’s time for chat and questions. We design our experiences for people who like to dig deeper. We finish up by Sydney’s spectacular harbour.

This is a great introduction to all things Sydney for cultural travellers. Even if you’re from Sydney, you’re bound to see and hear new things.
Check out our history and heritage walk of The Rocks Sydney; The Rocks – an alternative walking tour

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 since I studied at Sydney University. That’s a good thing. I’ve learned a lot from my recent reading. I’ve created a tour here that tells Sydney’s chequered story, while showcasing its stunning, photogenic, beauty.”

You can check the Rusty Compass independent travel guide to Sydney here.

Bara monument Sydney Harbour

Bara – In 2022 Sydney finally has a monument to its First Nations Peoples.© Mark Bowyer

The tour operates daily – check the schedule on the booking form. For special bookings, contact us at Put your own group together (min. 5). Send a booking using the form or email us.

The tour commences at 2.00PM (winter months) and concludes at 5.00PM . 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 ideas that have come up during the walk.

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.

$95 per person incl. 10% GST and one drink at a harbour-side bar.  Tours operate with a minimum 2 people. If we don’t have two travellers for a scheduled departure, the cost for a single (private tour) will be $190 incl. 10% GST. For other private tours, see below.

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

There are no entrance fees.

Sydney’s glorious Botanical Gardens – join us for a walk.© Mark Bowyer


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 2.5 – 3  hours with 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 most weather conditions – there is ample shelter along our route. 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 – even for locals.

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 Rum Hospital from 1816 Sydney

Possibly the first in Sydney’s chequered history of public private partnerships – a hospital funded by rum.© Mark Bowyer

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 8000 steps over 2.5 hours on mostly flat terrain. There are some steps. Families with younger children can organise a private tour.

We operate in most weather conditions – there is ample shelter along our route. 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 within 48 hours of travel.

Sydney colonial art

Early art of the colony – join us for a walk.© Mark Bowyer


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