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Offered languages
- English
This isn’t just a pub crawl — it’s Sydney’s history served with a drink in hand. Join us on a walking tour through The Rocks, stopping at four of the city’s most iconic heritage pubs. Along the way, you’ll hear true tales of convicts, larrikins, corrupt officials, and colourful locals who shaped the city — often over a pint. Enjoy a middy of beer, glass of house wine, or soft drink at each stop as you soak up stories of rum deals, razor gangs, and revolution. Led by a passionate storyteller, this is the past as you’ve never heard it: gritty, funny, and poured fresh.
What's Included
Meeting and pickup
Please meet on the harbour-facing side of the MCA, the large white building at Circular Quay. Your guide will be wearing a dark blue shirt, smart jacket, and BITS cap, near the steps facing the Opera House. Arrive 10 mins early — the tour departs on time.
the Tour finishes about 5 minutes walk from the meeting point in The Rocks. Trains, buses and ferries all within 5 minutes walk
Itinerary
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1
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.
15 minutes • Admission ticket free -
2
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.
20 minutes • Admission ticket free -
3
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.
10 minutes • Admission ticket free -
4
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.
5 minutes • Admission ticket free -
5
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.
5 minutes • Admission ticket free -
6
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.
20 minutes • Admission ticket free -
7
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.
5 minutes • Admission ticket free -
8
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.
20 minutes • Admission ticket free -
9
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.
20 minutes • Admission ticket free
Additional info
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Transportation options are wheelchair accessible
- Suitable for all physical fitness levels
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Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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Cancellation Policy
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
Rating
You can cancel up to 24 hours in advance of the experience for a full refund.
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