This self-guided adventure through The Rocks reveals the real Sydney, raw, rebellious, and absolutely fascinating.
Walk 3.3km through 18 historic sites where convicts, sailors, and survivors built a city from nothing. But you're not just seeing buildings, you're meeting the people who lived, loved, fought, and died here.
28 Captivating Audio Stories bring colonial Sydney to life. Hear about the families who thrived against impossible odds, the Green Bans, and of course the convicts
Discover what they ate, how they survived, and the legacies they left behind.
Total Freedom:
- Explore at YOUR pace, linger or breeze through
- Start anytime, morning, afternoon, or evening
- Pause, reread, replay, customize your route
- Experience history on your own terms
Perfect for:
Curious explorers wanting authentic stories, history lovers craving depth, really anyone who believes the best experiences reveal who made history, not just what happened.
Download the Guide, press play, and walk!
This is the starting point for your Self Guide Walk
The Gadigal people called this place Warrane. In 1788, eleven ships arrived carrying over a thousand desperate souls to an unknown land.
Built in 1845 by workers who knew every stone. Despite the the opinion of some, the First Fleet didn't land here—but generations of Sydneysiders have passed through its doors.
Mary Reibey arrived in chains at age 13. Isaac Nicolas was transported for theft. Both became respected businesspeople. How did they rebuild their lives from nothing?
For a century (1820s-1920), sailors, convicts, and locals drank side by side. Get arrested? The Police Station was next door. But the police were often as crooked as the convicts themselves.
The colony's first patients suffered here in canvas tents. Later, this narrow lane saw the colony's first street gangs clash.
Francis Greenway was transported for forgery, yet designed some of Sydney's most beautiful buildings. Can a criminal successfully return to his chosen profession?
Irish orphan girls, some as young as 14, arrived alone and terrified. Mary Driver was one. She made this street her home
Convicts chiseled through 140 metres of solid rock with hand tools. Every chip tells a story of backbreaking labor.
Long's Lane, Cribb's Lane, and Caracher's Lane - Beneath your feet: 33 homes where real families lived, loved, and struggled. Archaeologists found their cups, their toys, their secrets.
Edward Riley was an ex-convict. How did he afford these terrace houses? The answer might surprise you.
Jack Mundey mural - One union leader in the 1970s said "no." Without Jack Mundey's green bans, bulldozers would have erased all these stories.
Ann Smith, a convict nurse, ran away. For years, male convicts "nursed" the sick. Imagine being cared for by them.
Behind Harrington Street is Well Courtyard - William O'Neal's child drowned in this well. A parent's worst nightmare, preserved in stone.
Reynolds Cottages can be found here - 200 years old, built by convict hands, nearly demolished. The secrets of how they survived involve lies, luck, and determination.
Rest, refresh, and reflect on the people whose struggles built this place.
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All sales are final. No refund is available for cancellations.
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This experience is non-refundable and cannot be changed for any reason. If you cancel or ask for an amendment, the amount you paid will not be refunded.
You will not receive a refund if you cancel.
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