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Surry Hills & Darlinghurst History Tour — Gangsters, Girls & Grog

5 (5)
Haymarket, AU

Surry Hills & Darlinghurst History Tour — Gangsters, Girls & Grog

5 (5)
Haymarket, AU
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Step back in time and immerse yourself in the seedy underbelly of 1920s and 1930s Sydney on the Surry Hills & Darlinghurst History Tour — Gangsters, Girls & Grog. Uncover the dark secrets of the city's notorious criminal underworld as you explore hidden laneways and hear tales of vicious gang rivalries, cocaine addiction, and the sly-grog scene. But what sets this tour apart is the fact that the most powerful mob bosses were women. Tilly Devine and Kate Leigh ruled over their criminal empires, and their stories of power and control will leave you captivated. From the underworld of Surry Hills to the haunts and hideouts in Darlinghurst, you'll uncover the forgotten venues of these fierce Queens and the characters that surrounded them. Finish the tour on Stanley Street, where you can indulge in the speakeasy-style bars that still dot the area. With an intriguing itinerary and incredible historical insights, this tour is a must for curious travelers seeking an unforgettable experience.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • 2 hours 30 minutes
  • Suitable for 1-5 Participants
  • Small Group Tour, Private Tour
  • Guided Experience
  • Explore the secrets of Surry Hills and Darlinghurst
  • Meet the notorious characters of Sydney's underworld
  • Learn about the razor gangs, brothels, and illegal trades
  • Discover the hidden venues of Kate Leigh and Tilly Devine
  • Finish the tour in Stanley Street's speakeasy style bars
  • GST (goods and services tax)
  • 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
  • Gratuities
  • Food is not included on this tour, but your tour guide will have fantastic local recommendations

Popular Hotels Closeby

More about this experience


Transport yourself back in time to the notorious underworld of Sydney in the 1920s and 1930s with the Surry Hills & Darlinghurst History Tour — Gangsters, Girls & Grog. Step into the shoes of the women who dominated this era's criminal empires, Tilly Devine and Kate Leigh, as you explore the hidden laneways and secrets of Surry Hills. Discover the dark and gripping stories of working girls, gangsters, and hitmen who propelled Sydney into infamy. Brace yourself for an unforgettable journey through the labyrinthine streets of the 'Chicago of the South', where cocaine addiction, sly-grog operations, and vicious gang rivalries thrived. Dive into the lives of two powerful women who rose to the top of Sydney's underworld, defying societal norms and leaving an indelible mark on history. This immersive tour promises to take you on a thrilling and educational adventure through an era of crime, corruption, and extraordinary resilience.

What to expect?

Embark on a 150-minute tour filled with fascinating stories, intriguing history, and hidden secrets. Meet your knowledgeable guide at the iconic Sydney Central Station, from where the adventure begins. As you traverse the bustling streets of Surry Hills, you'll uncover the tales of the razor gangs, illegal grog-shops, brothels, and gambling joints that once frequented the area. Learn about the infamous crime-lords and ladies who ruled over this empire of illegal trades, painting a vivid picture of the roaring inter-war years. Finally, venture into Darlinghurst, once the playground of Sydney's underworld queens, Kate Leigh and Tilly Devine. Discover the forgotten venues of their sly grog and bordello empires, alongside the fascinating characters who kept them at the top of the food chain. The journey concludes on Stanley Street, surrounded by speakeasy-style bars and restaurants where you can continue your own exploration.

Who is this for?

This captivating tour is perfect for anyone with a passion for history, crime, and immersive experiences. Delve into the dark side of Sydney's past, where strong and formidable women ruled with an iron fist. Whether you're a history buff, a fan of true crime stories, or simply looking to uncover the hidden stories behind the city's vibrant façade, this tour is tailor-made for you. Join a diverse group of fellow explorers and embark on an adventure that celebrates the resilience and audacity of the women who defied societal norms to leave an indelible mark on Australian history. This tour is suitable for individuals, couples, friends, and families alike, making it an ideal outing for locals and tourists alike.

Why book this?

Take a step beyond the usual tourist attractions and dive into the riveting history of Sydney's underworld. This tour offers a unique and immersive experience that allows you to walk in the footsteps of the infamous characters who once roamed these streets. Gain insight into the lives of powerful women who defied expectations, overcoming obstacles to build vast criminal empires. This adventure promises thrilling stories, rich historical context, and an opportunity to see a different side of Sydney. Led by expert guides with a deep knowledge of the era, the Surry Hills & Darlinghurst History Tour guarantees an unforgettable and educational experience. Whether you're a local seeking to uncover the secrets of your city or a visitor with a thirst for the extraordinary, this tour is a must for those who crave a deeper understanding of Sydney's captivating past.

Good to know

During the Surry Hills & Darlinghurst History Tour, be prepared to do a fair amount of walking as you explore the hidden laneways and stories behind Sydney's underworld. The total duration of the tour is approximately 150 minutes, providing ample time to soak in the history and atmosphere. The meeting point is the Grand Concourse of Sydney Central Station, underneath the clock by the beautiful stained glass windows. Wear comfortable shoes and dress appropriately for the weather, as the tour operates rain or shine. Keep in mind that this tour involves discussions about illegal activities and the criminal underworld, so parental discretion is advised for younger participants. Prepare to be captivated by the underbelly of Sydney's past as you walk the city's streets and unravel the stories that shaped its history.


Feedback from individuals who have experienced the Surry Hills & Darlinghurst History Tour has been overwhelmingly positive. Participants express their appreciation for the tour's informative and engaging guides who bring the stories of Sydney's underworld to life. Many mention the excitement of exploring the hidden laneways and uncovering the secrets behind the city's infamous past. Travelers describe the tour as a unique and eye-opening experience that offers a fresh perspective on Sydney's history. The stories of Tilly Devine and Kate Leigh, in particular, captivate visitors, highlighting the tenacity and indomitable spirit of these women. Participants also value the tour's attention to detail and the opportunity to immerse themselves in the vibrant history of the city. Overall, the Surry Hills & Darlinghurst History Tour receives high praise for its educational, entertaining, and thought-provoking content.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Your Itinerary

Central Railway Station

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

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.



5 (5)


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.


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.

Mase T

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.


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.


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
Collected by Evendo, Tripadvisor & Viator
2024-04-23 18:28