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?
What to Expect
This self-guided walking tour in Sydney combines exploration, storytelling, and puzzle-solving into one unique experience. As you navigate through the city, you will discover 15 carefully selected locations, each revealing a piece of the story.
The entire quest takes approximately 7485 minutes to complete and covers 2.9km on foot. You will move at your own pace, with the freedom to pause whenever you want to take photos, grab a coffee, or simply soak in the atmosphere.
Each location features a challenge or puzzle that unlocks the next chapter of your story. These challenges are designed to be fun and engaging while teaching you about the history, culture, and hidden gems of Sydney.
No tour guide needed – your smartphone becomes your guide. The Questo app provides directions, shares stories, and presents challenges along the way.
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
Tips & Recommendations
Wear Comfortable Shoes
You will be walking throughout the city, so comfortable footwear is essential for enjoying the experience.
Charge Your Phone
Make sure your smartphone is fully charged. The quest runs through the Questo app, and you will be using it throughout.
Check the Weather
This is an outdoor activity. Bring an umbrella or sunscreen depending on the forecast.
Bring a Camera
You will discover photogenic locations and hidden gems perfect for capturing memories.
Stay Hydrated
Bring water, especially during warmer months or longer quests.
Play with Friends
While you can play solo, quests are more fun with friends or family. One ticket works for a group.
Important Information
Duration
Approximately 7485 minutes
Distance
2.9km walking
Group Size
Unlimited
Difficulty
Easy to Moderate
Accessibility
Not wheelchair accessible (stairs and uneven surfaces)
Cancellation Policy
Free cancellation up to 24 hours before your scheduled start time
Need to Know Before Booking
- •You will need the Questo app on your smartphone (iOS or Android)
- •Each ticket can be used by a group (share one device or play separately)
- •Internet connection required to download the quest initially
- •Once downloaded, you can play offline if needed
Ratings and Reviews
56 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 |
