Surry Hills & Darlinghurst History Tour — Gangsters, Girls & Grog
4.8
5 Ratings
Haymarket
Uncover the dark and intriguing history of Surry Hills and Darlinghurst, known as the 'Chicago of the South' in the 1920s and 1930s. Discover the stories of powerful female mob bosses, gangsters, and working girls on this immersive history tour.
Duration: 2 hours, 30 minutes
Cancellation: 1 day learn more
What's Included
  • Tour ends at Stanley Street, known for its speakeasy bars and restaurants
  • 2.5 hour guided walking tour of about 20 historical sites
  • Goods and Services Tax included
  • Visual folder with historic photos, maps, and portraits
  • Expert local historian as your guide
What's Not Included
  • Gratuities
  • Food is not included on this tour, but your tour guide will have fantastic local recommendations
Additional Information

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.

  • Not recommended for strollers
Location
Central Grand Concourse
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.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.8
(5 Ratings)
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Emm3cee
Nov 6, 2023
Brings history to life - Fascinating walking tour with Lucy around 1920s crime hotspots in Surry Hills and Darlinghurst. Informative and entertaining with loads of facts and stories of people that bring the locations to life. Good value for 2 hours.
Review provided by Tripadvisor
Therealroberto
May 2, 2021
History buff’s delight - A fascinating insight to another time brought to life by our enthusiastic and knowledgeable guide April. Walking in the footsteps of the legendary characters brought the stories to life. April’s commentary bordered on performance at times and her passion for the subject matter was clear and greatly enhanced the experience. Make sure you wear good walking shoes - it’s called Surry Hills for a reason. Well worthwhile.
Review provided by Tripadvisor
Karenecs
Jan 27, 2020
An infamous neighborhood and time brought to life. - Surry Hills is a great place for a walk through Sydney's esarly 20th century history. April is a passionate story teller who has done her research. She designed this tour and she has many historic photos of the people and buildings she includes in the walk--and those people and buildings are worth stories! Finishing up in an 'unmarked' basement sly-grog for a drink and a chat was the perfect ending to a very enjoyable afternoon.
Review provided by Tripadvisor
Dalwmark
Nov 23, 2019
Excellent - We had a great afternoon learning about the dark history of our own city. April, our guide was amazing - her knowledge and style made the trip extra special . Finishing with an Apple Whisky was also a plus. We are planning on going more walks with this company
Review provided by Tripadvisor
Mase
Nov 19, 2020
Backstreet legends of Sydney - Our guide was knowledgeable and enthusiastic and this made the tour fantastic. She took the time to tell stories in detail and answer any questions we had.... didn't feel like we were being rushed.
Review provided by Tripadvisor
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