Highlights of Sydney: From Prison to Freedom Land image 1

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

★★★★★Join 200+ explorers who unlocked Highlights of Sydney: From Prison to Freedom Land.
Quick start

Single Mission

Just looking for a single adventure?

Access: 1 Quest (Highlights of Sydney: From Prison to Freedom Land)
Devices: 1 device included
€9.99
Best for travellers

Sydney City Pass

The complete Sydney adventure.

Access: Top 7 Sydney Quests
Devices: 2 Devices Included
€39.99
Best value

Annual Pass

Play any quest in 1000+ cities for the price of a dinner for two.

Access: All 1000+ Cities Globally
Devices: 2 Devices Included
€79.99

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

Loading map…

About 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.

Good to know before you play

  • 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 at least 60% 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.

Ratings and Reviews

4.36

56 ratings

5 Stars
59%
4 Stars
25%
3 Stars
13%
2 Stars
0%
1 Star
4%
Reviews
Sort by

Wooyoung Chung

29 Jan 2026
It's very fun! I enjoyed very much!!!

Seokwan Chung

29 Jan 2026

Bree

20 Jan 2026

JMac and Fam

31 Jul 2025
a couple of clues were effected by building works and spelling mistake. overall a great way to take the kids around the harbour and learn about its history

Sarah Gale

14 Apr 2025
We had so much fun! Lots of amazing sights that we would never have found without the help of this game. Loved it!

Beat the best: Top Sydney explorers

coraSeeker
4600 XP
Niamh HookeySeeker
4600 XP
Vern Wingfield
Vern WingfieldSeeker
4600 XP

Compare Questo vs. Guided Walking Tours

Flexibility

Regular Guided Tours

Fixed schedules & no pausing

Questo

Start, pause, and resume anytime

Privacy

Regular Guided Tours

Crowds of up to 30 strangers

Questo

Private experience for your group only

Pricing

Regular Guided Tours

$30-$40 per person

Questo

Affordable per-group pricing

Availability

Regular Guided Tours

Requires advance booking

Questo

Instant access 24/7/365

Experience

Regular Guided Tours

Passive listening to a guide

Questo

Active gamification; you solve the mystery

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