Highlights of Sydney: From Prison to Freedom Land
🔒 Instant Access: Book now and start immediately. No need to wait for a guide.
⏱️ Total Flexibility: Start, pause, and resume whenever you want.
🧩 Gamified Discovery: Solve 15 location-based puzzles to unlock hidden stories and secret spots.
📍 Starting Point: Customs House, 31 Alfred St, Sydney NSW 2000, Australia
🛡️ Free Cancellation: Cancel up to 24 hours before your planned start for a full refund.
🌐 Available In: 🇬🇧 English
Places you will visit
15
It will take you
109-139 mins
You will walk
3810 steps
Total distance
2.9 km
Route you will explore
Starting point Customs House
31 Alfred St, Sydney NSW 2000, AustraliaFinish point Dawes Point
Dawes Point Reserve, Hickson Rd, The Rocks NSW 2000, AustraliaAbout this quest
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?
Highlights
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.
The mission: Your story in Sydney
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.
Landmarks & Hidden Gems Included
Observatory Hill
Campbell's Stores
Cadmans Cottage
Tank Stream Fountain
Customs House
- Best during the day
- Best for couples
Ratings and Reviews
55 ratings
Beat the best: Top Sydney explorers
Compare Questo vs. Guided Walking Tours
| Feature | Regular Guided Tours | Questo |
|---|---|---|
| Flexibility | Fixed schedules & no pausing | Start, pause, and resume anytime |
| Privacy | Crowds of up to 30 strangers | Private experience for your group only |
| Pricing | $30-$40 per person | Affordable per-group pricing |
| Availability | Requires advance booking | Instant access 24/7/365 |
| Experience | Passive listening to a guide | Active gamification; you solve the mystery |
