Team vs team
Use your own phones and join a team. Any teammate’s answer advances everyone. Beat the other teams on the leaderboard.
City exploration game
Highlights of Sydney: From Prison to Freedom Land
4.46Player ratingA DIFFERENT WAY TO SEE THE CITY
Play at your pace · usually 125 min 2.9 km Sydney App-guided
Play in
English
The experience
About this quest
Follow clues through The Rocks, Sydney and uncover the stories of the people who built this city. Discover the history of Sydney from the harbour to Observatory Hill, from Cadman's Cottage to the Garrison Church.
Step into the shoes of a former convict trying to make a new life in 19th-century Australia. This Sydney walking tour weaves Sydney's colonial history with a deeply human story of loss, survival, and belonging.
A self-guided walking tour of The Rocks unlike any other. Are you ready?
What makes this quest special
Highlights
- Discover popular and lesser-known places in The Rocks, Sydney's oldest neighbourhood.
- Experience how Lachlan Macquarie transformed Sydney from a penal colony into a proud colonial city in just over a decade.
- Step into the world of The Rocks Push gang and feel how dangerous these streets once were.
- Find a spiritual connection to this land and its people that will stay with you long after the walk ends.
From people who played this quest
Good times. In their words.
4.46 / 5
57 player ratings
Selected player reviews. Original words and ratings.
Most relevant starts with detailed five-star reviews. All ratings remain available.
From your phone to the streets
A walk that turns into an adventure.
- 1
Open the app. You’re on your way.
Choose your pass, then open your quest in the Questo app. It guides you from the starting point.
- 2
Get outside. Follow your curiosity.
Discover real places and their stories on foot. Stop for a coffee or a photo, then pick up where you left off.
- 3
Crack a clue. Share a little victory.
Look around for answers, solve puzzles and enjoy the “we got it!” moments.
CHOOSE YOUR PASS
How many are playing?
Get this questNo booking slot · play any dayFull refund until you start playing
BRING YOUR WHOLE GROUP
One city. Rival teams. Great stories together.
A school trip, a team day or friends out together. Turn your next outing into a little friendly competition.
Everyone for themselves
One player per phone. Solve clues on your own and race for the top spot on the final leaderboard.
Can a team share one phone?
Yes. Play together on one phone per team, or use your own phones and join the same team in the app. We recommend your own phones so everyone can take part.
Your walk, at a glance
Sydney
A · Start
31 Alfred St, Sydney NSW 2000, Australia
B · Finish
Dawes Point Reserve, Hickson Rd, The Rocks NSW 2000, Australia
Start and finish only. Discover the stops as you play.
Along the way
Landmarks & Hidden Gems Included
The people behind the adventure
Created by Ultimately Sydney.
A route that brings places and playful storytelling together.
Made by Ultimately Sydney
WHAT MAKES A QUEST DIFFERENT
Your adventure, with a playful twist.
1 / 4
Experience
- This quest
- Discover places through stories and clues in the app
- Guided walking tour
- Hear stories and ask a guide questions
2 / 4
Pace
- This quest
- Pause for a photo, a café or a longer look
- Guided walking tour
- Usually follows the guide’s schedule
3 / 4
Company
- This quest
- Explore with your own people or on your own
- Guided walking tour
- Private and shared group tours are available
4 / 4
Guidance
- This quest
- Directions and challenges in the Questo app
- Guided walking tour
- Live interpretation from a guide
Features and terms vary by experience. Check the details before booking.
Good to know before you play
- Best during the day
- Best for couples
A little clarity before you go
Frequently asked questions
Is Highlights of Sydney: From Prison to Freedom Land self-guided?
Yes. The Questo app guides you between locations without a tour guide or fixed departure. You can start when it suits you and pause if needed.
Where does Highlights of Sydney: From Prison to Freedom Land start and finish?
It starts at Customs House, 31 Alfred St, Sydney NSW 2000, Australia and finishes at Dawes Point, Dawes Point Reserve, Hickson Rd, The Rocks NSW 2000, Australia. The route is approximately 2.9 km and includes 15 location-based puzzles.
How many accesses does our group need?
This classic quest sells access per device and player. Each person who wants to solve clues on their own phone needs their own access.
What language is Highlights of Sydney: From Prison to Freedom Land available in?
It is currently available to play in English.
Keep exploring
Every quest. One year.
Explore the annual passGive them a story
A day out, gifted.
Explore Questo giftsKeep exploring Sydney
More adventures in Sydney
Colonial Sydney context
A penal colony that became a complex modern city
The British colony at Sydney Cove began in 1788 with transported convicts, soldiers and officials on lands already inhabited and cared for by Aboriginal peoples. Sydney’s later growth cannot be reduced to a simple journey from “prison to freedom.” This quest uses a personal story to explore colonial places while acknowledging both convict experience and the deeper Indigenous history of the harbor. Playable languages: English.
