Highlights of Sydney: From Prison to Freedom Land

4.21 (39 ratings)
Quest image more than 2

Follow clues to uncover the history of Sydney and discover the inspiring stories of the people of The Rocks, the stunning views from Observatory Hill, and the ruins at Foundation Park. Get in the shoes of a former convict trying to make a new life for himself in 19th-century Australia, a land of wonders and new possibilities. 

Are you ready to discover Sydney’s secret?


  • Can be played on
    Monday, Tuesday, Wednesday, Thursday, Friday, Saturday, Sunday

  • During these hours
    Whole day

  • Languages

Have an unlock code?


  • Discover popular and lesser-known places in Sydney.

  • Experience how, in only 11 years, Lachlan Macquarie rapidly transformed Sydney from a penal colony to a proud international city.

  • Hang out with ‘Push Gang’ members and imagine how dangerous The Rocks would have been.

  • Find a spiritual connection to Sydney that will stay with you forever.


You were a convict brought to Australia for the crime of stealing bread and butter from a shop back home in London. You were hungry at the time, unable to find work, and alone. Your only family, your mother, died two years before. You were in prison for 3 years, but today is your first day as a free man.  

What can you do? You feel lost and have no idea how to start a new life so far from home. You decide to visit Sydney as a free man for the first time. Maybe here you’ll find some hope.

Experience's route


Places you will visit


It will take you

109-139 mins

You will walk

3940 steps

Total distance

3 km

  • Best during the day
  • Instagrammable
  • Best for couples
People exploring Glasgow with Questo

Get the Questo app and you’re all set

Download it, choose your route and just walk to the starting point.

Download on the App StoreGet it on Google Play

Ratings and Reviews


39 ratings

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Sam Yan

15 Jun 2024
This is a really great game in a sense it compassed elements of crime, city walk, and history together. Totally worth a play! Question 4 was blocked by a construction place and not accessable. Q3 and Q10 really challening and even now I still don't know how was the answer concluded. Anyway very good game!

Vern Wingfield

09 Mar 2024
Great experience. is the tree name spelled wrong?


22 Jan 2024


11 Oct 2023


02 Oct 2023

What does a Questo Experience look like?

  • Walk and explore the Real-World

    Download the Questo app and choose your experience. Walk and follow clues to solve puzzles and unveil new locations and stories along the way.

  • Visit cities with Sightseeing Quests

    For your next trip, explore by going on a sightseeing quest without a guide. Enjoy the flexibility of starting and stopping the experience whenever you want, without the fear of missing out on the best places to visit or the best stories to learn.

  • Make your date memorable

    Invite your partner for a date, and go together on a fun walking adventure. Questo is a great date idea for couples that want to spend time together, but also for first dates or proposals.

  • Role-play in your city

    Attend a Questo Event, and immerse yourself in your favourite stories. Dress up in a costume for extra fun.


Vern Wingfield
4600 XP
Brent Kirpson-Colley
4588 XP
Shantel Gabriele
4517 XP