Convict Trails & Adventures, Sydney Walking Tour (Sydney Colony-History Walking Tour)

Covering a total area of 7.69 million square kilometres, mainland Australia is the world’s largest island – but smallest continent.

Australia is also the only continent that is governed as a single country. It is sometimes informally referred to as an ‘island’ continent, surrounded by oceans.

New South Wales is Australia’s oldest and most populated state. It was originally settled as a penal colony on the shores of Port Jackson where the bustling capital city of Sydney now stands. More than a third of Australians live in New South Wales, and Sydney is the nation’s largest city.

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Britain arrives and brings its convicts

A number of European explorers sailed the coast of Australia, then known as New Holland, in the 17th century. However, it wasn’t until 1770 that Captain James Cook chartered the east coast and claimed it for Britain. The new outpost was put to use as a penal colony and on 26 January 1788, the First Fleet of 11 ships carrying 1,500 people – half of them convicts – arrived in Sydney Harbour. Until penal transportation ended in 1868, 160,000 men and women came to Australia as convicts.

Today Australia is home to people from more than 200 countries. On our interesting “Convicts, Colony & History” tour you will learn the facts and tales behind Sydney’s stormed past.

Our Tour

Discover “Sydney as a local” and experience  it as the locals do by enjoying a beautiful day out exploring Sydney’s main iconic sites as well as the extensive harbour foreshore.

The earliest European Sydneysiders, convicts, soldiers, whalers and sailors, all walked this route. Later came the shipping magnates, wharf labourers and traders. The Rocks and Millers Point have been overlaid by generations of change. But amongst the bustling modern city streets, remnants and traces of these early times can be found. Pubs and churches, archaeological digs and houses all evoke memories of past lives, past ways.
What You’ll Do
  • Get an insider’s perspective on Australia’s Colonial History by your local Ringer*
  • Run by a “Fair Dinkum” Australian tour guide
  • Learn about Convicts, Gangs and Pubs
  • “Ringer*” the best available
Take a walking tour of the city’s most popular monuments and bustling piazzas starting from the Customs House where shipping was cleared and goods passing through the port of Sydney were taxed and cleared for sale or export, to Millers Point , a precinct where old 19th century sandstone buildings live side-by-side with red brick structures created in the first decades of the 20th century by the Sydney Harbour Trust. Walk through The Rocks, where the first settlers arrived and see how everyday life was during those first years.
During our  walking tour we will admire historical buildings and learn about:
  • Australia’s Colony History
  • The Rocks – How it all started
  • Convicts, Gangs and Pubs
  • Cadman’s Cottage
  • The Colony – story of survival
  • The “Rum” Rebellion
  • Sydney Harbour Bridge
  • ‘Rum’ Hospital
  • Aboriginal History
  • Suez Canal and Nurses Walk
  • Museums and Galleries
  • What to do in Sydney and many more, plus get useful tips on where to go and what to do from our local guide.


Price: 1-2 people $240

1-4 people $300

1-6 people $400

          What’s included

  • Local licensed guide
  • 2 to 2.5 hour Sydney walking tour
  • Learn about Convicts, Gangs and Pubs
  • Enjoy the Informative commentary of your Ringer* tour guide
  • You’ll get a vocabulary lesson on Aussie slang throughout the tour
  • Get all the inside gossip of the early history of what was once a Penal Colony and is now a thriving international city.
  • Discover the importance of Customs House in molding the City of Sydney
  • Find out why the eastern suburbs is still the wealthiest part of Sydney city

          What isn’t included

  • Entrance fees
  • Hotel pick-up and drop-off
  • Food and beverages (not mentioned)
  • Gratuities/Tips (optional)
  • Coffee/tea purchases
  • Food purchases
  • Drink purchases
  • hotel pick-up & drop-off:
  • Group bookings only by request
I did the Sydney (Australia) walking tour today and it was much better than what I have expected!!
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Better than I had expected!!!

Check Availability

  • Location: Meet at Customs House,31 Alfred Street, Circular Quay, Sydney NSW 2000
  • Departure time : 10:00 a.m
  • Walking pace: Easy

Notes & Clarifications

Keep in mind that if you select a private tour, it is possible to customize it to meet your desires.

Should you want to change the itinerary please do not hesitate to contact us by sending us a request through the inquiry form.

Weather: In the event of potential inclement weather, the threat of weather or natural disasters, on the day of a scheduled tour, the tour will be canceled or postponed. For more info: Booking Terms and Conditions

Dress Code : Please wear comfortable walking shoes and bring your camera! And an umbrella just in case!


If you are happy with the services provided by your local guides a tip – though not compulsory – is appropriate. While it may not be customary to you, it is of great significance to the people who will take care of you during your travels, inspires excellent service, and is an entrenched feature of the tourism industry across many world destinations. Please consider this when budgeting for your extra expenses on this tour.

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Office Phone number: +61406671948
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Available departures

This is a daily tour.

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