Historical Sydney pub tours uncover the city’s past

Sydney’s pubs have always played a prominent and sometimes infamous role in the social fabric of our oldest city, with smugglers, illegal betting and the 6 o’clock swill just some of the more colourful chapters. Explore Sydney’s oldest and most atmospheric pubs and bars on this 'Ultimate Sydney Historic Pub Crawl'. Review: Roslyn Jolly

Sydney pub tours
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These historical Sydney pub tours visit four of the city’s oldest and most famous public houses and bars. Enjoy great beer (own expense) and tasty included bar snacks, and listen to the stories and histories of these fascinating watering holes.

Tour name: Ultimate Sydney Historic Pub Crawl
Runs: Wednesday to Sunday
Departure point: CBD
Departure time: 6pm
Duration: 4 Hours (approx.)
Inclusions: Guided walking tour, commentary and bar snacks

Best price guarantee: If you find this tour elsewhere at a cheaper price, we will beat it by 10%. Some conditions apply. There are no booking or credit card fees when you book this tour with The Big Bus tour and travel guide.

Do you know the origin of the phrase ‘as happy as Larry’?

Where you can hear birdsong in the city both day and night? Where the proceeds of Australia’s first bank heist are thought to be buried? If you answer ‘no’ to any or all of these, join Go Local Tours’ Ultimate Sydney Historic Pub Crawl. By the end of the evening you’ll have all the answers, along with many other insights into the city’s social history. You’ll also have spent time in some of Sydney’s finest historic drinking establishments, including three of the top contenders for the title of the city’s oldest pub. The atmospheric Lord Nelson, established in 1841, is still trading in its original building.

Encompassing four pubs over the course of four hours, these Sydney pub tours start in the CBD near the Queen Victoria Building and finish at Millers Point. That’s about two kilometres of walking, including a couple of hills and some stairs, so wear comfortable shoes.

The pub stops are leisurely, with plenty of time to buy a drink at each one and soak in the ambience. Hot finger food, included in the tour price, is served at the third pub – we were offered slices of gourmet pizza and potato wedges, and were glad of the opportunity to recharge at that point. (Hint: have a snack or early dinner before the 6pm departure, to keep your energy up over the first two hours.)

Sydney pub tours

Sydney pub tours. Image courtesy of The Lord Nelson Brewery Hotel

There were seven other guests on our pub crawl. Our companionable guide, John, offered an extensive commentary, not just on the pubs, but also on other buildings and points of interest along the route. This information was part of a narrative that included a fair amount of convict and colonial history, stories of Sydney’s civic life in the nineteenth century, and an account of the union-led Green Bans that saved The Rocks from overdevelopment in the 1970s. There’s an emphasis on ‘characters’ from the city’s turbulent past, and a sprinkling of paranormal elements just to spice things up.

For me, one of the great pleasures of the tour was being led down laneways, backstreets and staircases I would never have thought of going down, and perhaps would not have known existed. A tiny alleyway in The Rocks was just the place to hear how Sydneysiders were terrorized by members of The Push, a gang of roughs who ruled the city streets in Victorian times.

The poverty of nineteenth-century labouring families came vividly to life when we stood within the miniature rooms of the catacomb-like houses they had carved out of the sandstone cliffs near the harbour. Only a block from busy George Street, stone-paved lanes – now home to restaurant tables set for elegant dinners – recapture the feel of the city before it was taken over by traffic. (Imagine that!)

Sydney pub tours

Sydney pub tours: Explore the colonial history of The Rocks. Image: Photodune

A highlight of the evening was our descent into the underworld of The Hero of Waterloo pub. This is a truly eerie ‘off-limits’ experience not available to regular patrons. Much to my surprise, we discovered that it wasn’t a flight of fancy that led John to describe the pub’s cellar as a dungeon.

The underground space really is just that, a place of iron gates and chains and stone cells. Unwitting guests, lured to the hotel by offers of free rum, were ‘shanghaied’ here – in a deal with ships’ captains. The publican plied guests with drink, imprisoned them overnight and delivered them next day by secret tunnel directly to ships waiting in the harbour, which would then spirit away these befuddled, press-ganged additions to their crews!

Sydney pub tours

Sydney pub tours. Image courtesy of The Hero of Waterloo

Thankfully, this sombre story was balanced in the course of the evening by plenty of lighter tales of bets and booze-ups, best mates and bare-knuckle fights. We heard about the man whose friends bought him a pub, the convicts who robbed the bank they were assigned to build, and the sculptor whose statue of Queen Victoria was considered too racy to put on display. We also got to see some really lovely historic buildings and enjoy a range of unusual craft beers.

And how did we feel after all that? As happy as Larry.

Roslyn travelled as a guest of Go Local Tours.

Additional images: Bigstock


Roslyn Jolly

About the writer

Roslyn Jolly is a freelance travel writer whose work has appeared in Luxury TravelGet Up & GoThe Sunday Telegraph (Escape) and The Australian (Travel & Indulgence). In her former career as an English Literature academic, she studied and taught the work of great travel writers, such as Henry James, Herman Melville and Robert Louis Stevenson, and became fascinated by the history of travel and tourism. Two years at school in Wales and three years at university in England allowed her to travel extensively in Europe and North America, which she continues to do. On a trip to Borneo in 2015, her eyes were opened to the wonders of Asia. Her most amazing travel experience so far was looking into the eyes of a Bornean gibbon spotted in the rainforest canopy in Brunei. Dream destinations for the future include Antarctica, Mongolia, Bhutan, Namibia, Iceland and Greece – and seeing more of Australia’s north and west.

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