Sydney – tales of the city
A walking tour of Sydney history and stunning scenes
Sydney – tales of the city
Sydney – tales of the city
Sydney – Tales of the City is a private heritage walking tour through Sydney’s extraordinary past – concluding right by Sydney Opera House and Sydney Harbour Bridge on Sydney Harbour. We experience the stunning beauty, the history, architecture, art and energy of Australia’s oldest and largest city. Explore spectacular Sydney, its gardens, its harbour and monuments.
Our walk is focused on the period that follows the colonial invasion of 1788 and the beginnings of the dispossession of Australia’s First People, with 60,000 years of heritage on the continent. We examine how a violent penal colony was transformed into one of the world’s most admired modern cities.
Our walks share big stories, beautiful scenes – with a sense of humour. They inspire interesting Sydney conversations. We can also help you make the most of your stay here with ideas and suggestions.
Send us a booking at [email protected] or message us in Sydney on 042663864. Ask us about customised tours and tours for families.
Check out our independent Sydney travel guides at our sister brand Rusty Compass, here.
Tour highlights - Sydney tales of the city
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 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
You can check the Rusty Compass independent travel guide to Sydney here.
AUSTRALIAN HISTORY IN 2025
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 and their history of dispossession since colonisation.
If you would like to think more about these issues, we recommend
OUR TOUR LEADERS
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.
ABOUT YOU
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.
WHEN DOES THE TOUR OPERATE?
The tour operates any day based on availability. Commencing at 3.00PM in summer months and 2PM in winter. Including breaks the tour runs for approximately 3 – 3.5 hours. The tour can also operate in the morning (from 8.30AM) We time our walks for picturesque light and we finish with a drink (included) 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.
WHAT’S INCLUDED
Expert guide, harbour-side drink, presentation. Private tour experience.
CONDITIONS
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 6000 steps over 2.5 hours on mostly flat and shaded 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 48 hours prior to the tour without penalty. There are no refunds for cancellations within 48 hours of travel.
CUSTOMISED PRIVATE TOURS
For special groups, student groups and families, contact us at [email protected]. You can put your own group together and we can talk about your special interests. We love photography, architecture, coastal walks and more.
GADIGAL COUNTRY
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.
WHAT TO BRING
Comfortable walking shoes, hat, sunscreen, water bottle and warmth in winter, umbrella and raincoat when conditions require.
Tour Brief
Private history walking tour of Sydney – expert leaders, history, architecture, parks, gardens and stunning, Sydney scenes.
- $640AUD per group (1 – 5 people) incl. GST drinks and snacks. Ask about pricing for larger groups. Recommended for adults and children older than 12.
- Expert led – Sydney and Australia insights – history, architecture, politics and culture.
- Operates any day by prior booking. Recommended timings for light and weather conditions – Summer – 8.30 – 11.30 (approx) OR 3.30 – 6.30 (afternoon recommended in summer). Winter – 9 AM- 12PM OR 2PM – 5PM (approx).
- Email: [email protected] / Call or WhatsApp +61426638642
- Mobility essential – up to 8000 steps (ask about customised walks with fewer steps.
- Ask about customised walks of architecture, art, neighbourhoods, beaches, historic houses and Sydney’s National Parks.
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