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

Sydney , Australia

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

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(6 reviews)

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About this experience

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.

Available options

New start time

What's included

Tour finishes on Stanley Street. a great place filled with speakeasy bars and restaurants

GST (Goods and Services Tax)

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

Detailed itinerary

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.

What's not included

Gratuities

Food is not included on this tour, but your tour guide will have fantastic local recommendations

Available languages

Guide guide

Reviews breakdown

Tripadvisor 4.8

6 reviews

5★

4★

3★

2★

1★

Important information

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

Meeting point

Please meet outside the **old Excelsior Hotel, El Loco at Excelsior** on 64 Foveaux Street. A short stroll from Central Station.

About Sydney

Sydney, Australia's most iconic city, is renowned for its stunning harbour, vibrant cultural scene, and diverse neighborhoods. With its blend of natural beauty, historic landmarks, and modern attractions, Sydney offers an unforgettable experience for every traveler.

Top Attractions

Sydney Opera House

An iconic landmark and UNESCO World Heritage site, the Sydney Opera House is a masterpiece of modern architecture and a hub for performing arts.

Architecture/Cultural 1-2 hours for a tour, longer for a performance AUD 42-100 (tour prices vary)

Sydney Harbour Bridge

One of the world's most famous bridges, offering spectacular views and the thrill of the BridgeClimb or BridgeWalk.

Architecture/Adventure 2-3 hours (depending on activity) AUD 174-468 (BridgeClimb prices vary)

Bondi Beach

Australia's most famous beach, known for its golden sand, surfing, and vibrant atmosphere.

Beach/Entertainment Half day to full day Free (surfboard rentals and lessons cost extra)

The Rocks

A historic area with cobblestone streets, colonial buildings, and a vibrant market scene.

Historical/Cultural 2-3 hours Free (market and museum entry fees apply)

Royal Botanic Garden Sydney

A beautiful oasis in the heart of the city, offering stunning views of the harbour and Opera House.

Nature 1-2 hours Free

Must-Try Local Dishes

Avo on Toast

A simple yet iconic dish featuring avocado on toast, often topped with poached eggs, feta, or smoked salmon.

Breakfast Vegetarian (check for specific toppings)

Barramundi

A popular Australian fish, often grilled or pan-fried and served with seasonal vegetables and a sauce.

Dinner Gluten-free (check for specific sauces and sides)

Tim Tams

A beloved Australian chocolate biscuit, often enjoyed with a cup of tea or coffee.

Snack Contains gluten and dairy

Flat White

A popular Australian coffee, similar to a latte but with a stronger coffee flavor and velvety microfoam.

Drink Contains dairy (non-dairy options available)

Popular Activities

Hiking in the Blue Mountains Surfing at Bondi Beach BridgeClimb or BridgeWalk at Sydney Harbour Bridge Kayaking in Sydney Harbour Scuba diving in Jervis Bay Beach lounging at Bondi Beach Picnicking in the Royal Botanic Garden Spa day at a luxury hotel

Best Time to Visit

December to February (Summer)

Summer is the peak tourist season in Sydney, with long, sunny days perfect for beach activities and outdoor events. However, it can be crowded and more expensive.

20-26°C 68-79°F

Practical Information

Language

Official: English
Widely spoken: English, Mandarin, Arabic, Cantonese
English: Widely spoken

Currency

Australian Dollar (AUD)

Time Zone

AEST (GMT+10) or AEDT (GMT+11) during daylight saving time

Electricity

230VV, 50HzHz

Safety Information

Overall Safety Rating: Generally safe

Sydney is generally safe for travelers, with low crime rates and a welcoming atmosphere. However, as with any major city, it's important to stay aware of your surroundings and take precautions to ensure a safe and enjoyable trip.

Important Precautions:

• Keep valuables secure and be cautious in crowded areas.
• Use licensed taxis or ride-sharing services to avoid overcharging.
• Purchase tickets from official sources or authorized sellers.

Getting there

By air

Sydney Kingsford Smith Airport • 8 km (5 miles) from city center

By train

Central Station, Sydney Terminal

By bus

Central Station, Sydney Terminal

Getting around

Public transport

Sydney's train network is efficient and covers most of the city and surrounding areas.

Taxis

Available • Apps: Uber, DiDi

Rentals

Car, Bike, Scooter

Neighborhoods

The Rocks Bondi Surry Hills Newtown Barangaroo

Day trips

Blue Mountains

80 km (50 miles) from Sydney • Full day

A stunning national park known for its dramatic landscapes, waterfalls, and scenic hiking trails.

Hunter Valley

120 km (75 miles) from Sydney • Full day

Australia's oldest wine region, offering beautiful vineyards, wine tasting, and gourmet dining.

Royal National Park

30 km (19 miles) from Sydney • Half day to full day

Australia's oldest national park, offering beautiful coastal scenery, hiking trails, and wildlife spotting.

Festivals

Sydney Festival • January Sydney Gay and Lesbian Mardi Gras • February/March Sydney Writers' Festival • May

Pro tips

Use an Opal card for convenient and discounted public transport fares.
Visit iconic attractions like the Sydney Opera House and Harbour Bridge early in the morning or late in the afternoon to avoid crowds.
Explore Sydney's diverse neighborhoods, each with its unique character and attractions.
Take a ferry to explore the city's stunning harbour and waterfront areas.
Try local specialties like seafood, Asian cuisine, and Australian wines.