Convict Trails and Adventures - Historic Sydney Walking Tour

Sydney, NSW
For 2



or 4 fortnightly payments of $0

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  • Explore Sydney's famous sites and landmarks
  • Learn the history starting from the first settlers
  • Hear stories on convicts and gangs

Discover Sydney as a local and retrace the steps of convicts, soldiers, sailors, labourers and traders. Listen to incredible stories of Australia's Colony History; of prison life, Aboriginal displacement and the gold rush era. Visit iconic buildings and learn the stories behind their existence.

Why You'll Love This

What's Included?

  • Learn about Australia's Colony History
  • Learn about the major moments in history that shaped Sydney
  • Hear amazing stories about the adventurous migrants from Europe
  • Visit historical buildings and famous landmarks
  • Knowledgeable and engaging tour guide
  • A beer at Sydney's oldest Pub

During this walking tour you will learn about Australia’s Colony History. Explore The Rocks and hear how it all started. Listen to the Australian story of survival, tales of convicts and gangs and the Aboriginal history. You will visit major landmarks, 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.

The earliest European Sydneysiders, convicts, soldiers, whalers, sailors and traders all walked this route and while The Rocks and Millers Point have been overlaid by generations of change, amongst the bustling modern city streets, remnants and traces of these early times can be found. This is a fantastic tour of adventure and discovery for locals and visitors alike. Your guide will give you many useful tips on where to go and what to do in Sydney as well as provide you with refreshments half way through the walking tour.

On the Day

Session Length

  • Please allow approximately 2.5 - 3 hours for this experience
  • Available seven days a week
  • Available on public holidays only upon request
  • Departure time is at 10:00 a.m

Numbers on the Day

For experience in Group, participants can be up to 12 people (but 4 - 5 participants for the best experience is recommended).


In the event of rain or inclement weather your experience may be cancelled. You will be contacted by the experience provider and rescheduled.

Dress Code

Please wear comfortable walking shoes and bring your camera

... and Importantly


  • This experience is suitable for all levels of walking ability although it does involve a fair amount of walking
  • Children up to 12 years of age participate for free
  • Persons over the age of 12 are obliged to pay the adult rate


Once this experience has been confirmed, changes are at the discretion of the experience provider and are arranged directly with them according to this policy:

  • No charge if cancelled within 1 week of tour
  • Full refund minus 15% administrative fee if cancelled within 2-6 days of tour
  • 50% cancellation fee if cancelled within 24 hours of tour
  • No shows, Late Arrivals and same day cancellations: participants forfeit their experience and therefore are not entitled to a refund or re-book. Participants are advised to make their own insurance provisions in case of unforeseen circumstances.