Sydney – tales of the city

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, its harbour and monuments, 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 (over 12 years) incl. GST and harbourside drink. Commences 2PM – ends around 4.30 – 5PM (April to October) with option to stay longer for chat. Our walks inspire great Sydney conversations.

Send us a booking at [email protected] or call us in Sydney on 042663864. Ask us about customised tours and tours for families

Tour highlights

Botanical Gardens, Sydney
Botanical Gardens, Sydney © Mark Bowyer



* 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 Sydney from convict colony to the present – from gardens and the harbour to grand Victorian and contemporary architecture.
* 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 relationship with the harbour – where the dispossession of Australia’s First Peoples began in 1788.
* 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 into history and society. 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

The oldest church in central Sydney - walking tour Sydney Tales
Designed by a convict, built by convicts - the oldest church in central Sydney ©Mark Bowyer


The telling of history is always evolving. We discover new facts. We look at the same facts from a different perspective. 

Like many countries, Australians are facing up to some challenging facts in our history. It’s proving a fraught process. We seek to operate our walks in a way that respectfully acknowledges Australia’s First Peoples.  


Old Compass Travel tour leaders are experts in the places they work. They bring depth to our walks well beyond the talking points of the itinerary. They’ll have an interest in history, politics and contemporary affairs, architecture and economics – big stories. They’ll also be able to help you make the most of your Sydney and Australia travels.


You’re a curious, active traveller (over 12 years of age – – ask us about private family tours) 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.  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.

Royal Botanical Gardens and the modern Sydney skyline
Royal Botanical Gardens and the modern Sydney skyline © Mark Bowyer


The tour operates daily – check the schedule on the booking form.

The tour commences at 3.00PM (summer months) and 2PM in winter and concludes at around 6.00PM or 5PM. We time our walk for light and 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 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 best afternoon light and conditions.


$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, harbour-side drink, presentation. Small group (max 8) experience.

Curious statues of Sydney © Mark Bowyer


The tour is available to anyone over 12 years of age with average fitness and mobility (ask us about family walks and walks for the less mobile). We walk around 8000 steps over 2.5 hours on mostly flat terrain. There are some steps.

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.

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


For special groups, student groups and families, contact us at [email protected]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.

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


Comfortable walking shoes, hat, sunscreen, water bottle and warmth in winter, umbrella and raincoat when conditions require.

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

Tour Brief

  • $95AUD incl. GST (adult / child over 12 years)
  • Operates Daily: 2pm –  5pm including breaks and drinks (autumn / winter)
  • Call us on +61426638642 or email [email protected]
  • Minimum: 2 people – min. age 12.
  • Drink by the harbour and expert guide included
  • Ask about family and private walks

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