History on Tap
The Story (Dingo’s voice, straight-up history with cheek): Sydney wasn’t founded on marble halls or grand ideals. It began in 1788 when the First Fleet dumped over 1,400 convicts, soldiers, and officials onto the land of the Eora people. What followed was less “Empire glory” and more wild experiment — a city forged in conflict, chaos, and the occasional drunken brawl.
There was no currency, barely any law, and plenty of desperation. Rum became money. Gangs ran laneways. Sailors were kidnapped by press gangs. Convicts plotted escapes into the bush. Bushrangers turned the colony into their stage. For eighty years, Sydney was the most dangerous port in the British Empire — part frontier, part prison, part madhouse. And yet — from that anarchy came the spark of Australia’s spirit: mateship, rebellion, cheek, and survival.
What You’ll Discover on the Tour:
1.Rumocracy
How booze became currency and toppled a Governor in the infamous Rum Rebellion.
2.Law vs Chaos
From the six o’clock swill to sly-grog shops, Sydney kept drinking - no matter what rules were thrown at it.
3.Port City Perils
Press gangs, smuggling, gang wars, and convict escapes that
shaped The Rocks into Sydney’s roughest neighbourhood.
4.Culture Clash
Where convicts, soldiers, sailors, and Indigenous people collided - sometimes violently, sometimes in ways that shaped the city’s character forever.
What to Expect:
Quick Tips:
1
This is history with flavour - pace yourself, it’s a story not a session.
2
Respect the venues - they’re part of Sydney’s living history.
3
Stick together in the laneways - even sober people have gotten lost here.
4
Bring ID and comfy shoes - cobbles + chaos require balance.
Don’t Just Visit Sydney. Roam Its History.
Small groups. Big stories. Tours that sell out fast — slip the leash and join the pack.
