Why choose this Sydney tour ?
Known as the ‘Chicago of the South’ Sydney in the 1920s and 1930s was famous for its vicious gang rivalry, cocaine addition, and sly-grog scene.
From this labyrinth of lanes a mass of criminal empires emerged, ruled by two mob bosses with a difference – these bosses were women. Hailed Queens of the Underworld, Tilly Devine and Kate Leigh, had crawled their way up from obscure origins over the bodies (sometimes literally) of men to become the most powerful women in Sydney, and they were not about to give up that power — especially not to each other.
Join us as we explore the lesser known laneways and secrets of Surry Hills, meet the colourful collection of working girls, gangsters and hit men who gave Sydney a bad reputation, finishing on Stanley Street a popular street with many speakeasy style bars.
Make the most of your Sydney adventure
What makes Surry Hills & Darlinghurst History Tour — Gangsters, Girls & Grog a unique experience ?
Meet your guide in the Grand Concourse of Central Station — a large terminus hall constructed in the early 1900s with a giant steel frame vaulted roof. Your tour guide will introduce you to the notorious characters that preyed on naive newcomers who once arrived here on the country trains.
You’ll also learn what happened here in 1916 that helped determine Sydney’s underworld over the next decades.
As you walk through the history of the area you’ll learn about the notorious razor gangs, illegal grog-shops, brothels, gambling joints and slums. You’ll also delve into the stories of the infamous crime-lords and ladies who ruled over an empire of illegal trades scattered throughout Surry Hills streets and alleyways in the roaring inter-war years.
Darlinghurst was once the playground of Sydney’s not-so-glamourous underworld Queens : Kate Leigh & Tilly Devine. You’ll discover the forgotten venues of their competing sly grog & bordello empires and the cocaine-crooks, standover men, gangsters, good-timers, haunts & hide-outs that kept them at the top of the food-chain.
Tour Description & Additional Info:
- Public transportation options are available nearby
- Not recommended for travelers with spinal injuries
- Not recommended for pregnant travelers
- Suitable for all physical fitness levels
- Not recommended for strollers
Options To Choose for Your Trip:
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Surry Hills & Darlinghurst History Tour — Gangsters, Girls & Grog Inclusions:
Included with Your Ticket
- Tour finishes on Stanley Street. a great place filled with speakeasy bars and restaurants
- 2.5 hour walking tour covering approximately 20 historic sites and stories
- A visual folder with historic imagery, maps and portraits of the area
- A local Sydney historian as your tour guide
- Food is not included on this tour, but your tour guide will have fantastic local recommendations
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Special Instructions:
- This Tour is Provided by Journey Walks.
- Tour Timezone & Starts at Australia/Sydney.
- Mobile or paper ticket accepted.
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- This Tour is Rated 5 Stars based on 5 valid reviews on TRIPADVISOR.
- Minimum 1 Travelers is required to book.
- Maximum 5 Travelers is accepted for booking.
