Where the Chaos Began Built in 1816 on Sydney’s original shoreline, this was the landing point for illegal grog, smugglers, and shady deals. Home to a convict-turned-coxswain, it sat at the heart of the harbour’s black market. If Sydney had a ground zero for mischief — this was it.

Since 1828, this pub has been pouring drinks, settling scores, and sheltering scoundrels. It served soldiers, sailors, and anyone with a thirst and a story. Inside? War memorial meets watering hole. Outside? The Rocks’ history soaked into the floorboards — and possibly the carpet.

Once an opium den, bootmaker’s shop, and cheap lodging house, this 1840s sandstone cellar now serves whisky where drunks once slept it off. It’s heritage with a hangover — a place where Sydney’s underclass once paid a penny for a bed… or a bottle.

This tight sandstone alley was once Australia’s most dangerous shortcut. Push gangs prowled the shadows, rolling sailors and slashing rivals. Locals gave it a wide berth — ironic, given it’s the narrowest laneway in the country.

Convicts carved this tunnel through solid rock with picks, chains, and fury. When progress stalled, the government brought in gunpowder. It’s the only shortcut in Sydney built on hard labour, blasted rock, and very bad moods.

This heritage pub has been pouring pints since 1901. During the era of the six o’clock swill, thirsty Sydneysiders packed the bar shoulder-to-shoulder, necking beers before closing time. It’s one of the last places in The Rocks where you can drink in real history.

This archaeological site unearthed over 1,000,000 artefacts and the remains of 30 convict-era homes — including one with a secret backyard distillery. Hidden booze, buried bones, and Sydney’s scrappy beginnings all lie just below the surface.

Sydney’s oldest licensed pub, still pouring since the 1840s. Built by convicts, run by characters, and home to more than one ghost story — this place has sandstone walls, a working brewery, and the kind of bar where history sticks to your boots.

Built in 1843 and soaked in scandal ever since. This pub's sandstone walls hide tales of press gangs, trapdoors, and tunnels to the harbour. Some say drunken sailors woke up at sea. Others never woke up at all. Come for a drink, stay for the legends.