Overview
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.
- Recommended by 98% of travelers
- Badge of Excellence
- Free cancellation up to 24 hours before
- Mobile ticket
What's included
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
Goods and Services Tax (GST)
A visual folder with historic imagery, maps and portraits of the area
A local Sydney historian as your tour guide
Gratuities
Food is not included on this tour, but your tour guide will have fantastic local recommendations
Meeting and pickup
Travelers meet at the meeting point.
Meeting point
Your guide will meet you in the Grand Concourse of Sydney Central Station (the main terminus hall).
Look for the large hanging clock in the centre of the Grand Concourse — your guide be located underneath this clock, by the stain glass windows that face the 'Next Departure' screens.
End point
This tour finishes with on Stanley Street, a great place with many speak-easy style bars and restaurants.
Surry Hills, Hyde Park & Oxford Street n are all with in walking distance of this location with bus and train routes that run to and from the city.
What to expect
-
Central Railway Station
15 min
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. -
Surry Hills
1 hour
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
1 hour
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.
Cancellation Policy
For a full refund, cancel at least 24 hours before the start time.
Times are local to the experience (Australia/Sydney).
Additional Information
- Not recommended for strollers
- Mobile or paper ticket accepted
- Up to 5 travelers per booking
FAQs about Surry Hills & Darlinghurst History Tour — Gangsters, Girls & Grog
Can I cancel Surry Hills & Darlinghurst History Tour — Gangsters, Girls & Grog for free?
Yes. For a full refund, cancel at least 24 hours before the start time.
How long does it take?
It takes about 2 hours 30 min.
Where does it start?
Your guide will meet you in the Grand Concourse of Sydney Central Station (the main terminus hall).
What's included?
- 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
- Goods and Services Tax (GST)
- A visual folder with historic imagery, maps and portraits of the area
- A local Sydney historian as your tour guide
What's not included?
- Gratuities
- Food is not included on this tour, but your tour guide will have fantastic local recommendations
Which places does it visit?
It visits Central Railway Station, Surry Hills, Darlinghurst.
Which languages is it offered in?
It is offered in English.
Operated by Journey Walks
