Adventure Collective
Sydney’s Convict Colony Walk with Journey Walks - Sydney

Sydney’s Convict Colony Walk with Journey Walks

Sydneyeasy

Difficulty

easy

Duration

2.5 hours

Fitness Level

Suitable for most fitness levels; the walk includes staircases and some uneven cobblestones requiring good balance.

Overview

Walk the storied lanes of Sydney’s Rocks district with Journey Walks. Uncover convict legacies, hidden ruins, and rugged colonial tales on this 2.5-hour history tour.

Redfern, New South Wales

SYDNEY’S CONVICT COLONY – A WALKING HISTORY TOUR OF THE ROCKS

Ages 12+ • 2.5 hours • Historian Guide • Over 1000 five star reviews • Small tour (max 15 guests)

History Tour

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About This Adventure

Embark on a captivating 2.5-hour walking tour through Sydney's historic Rocks district, where tales of convicts, colonists, and rum come alive. Led by engaging local historians, uncover hidden alleyways, ancient ruins, and the secrets of the first settlement. Experience history like never before, filled with humor and intriguing stories.

THE INCREDIBLE STORY BEHIND SYDNEY’S ORIGINAL SETTLEMENT OF THIEVES, RUM AND RED-COATS

Minimum booking of 2 required to unlock single bookings

Duration

2.5 Hours

Expect

Fascinating history, delivered with energy and insight as we uncover the scallywag stories of convicts, colonists, soldiers, sailors, larrikins, legends, rum and rebellions!

Tour Info

Once upon a time (not so long ago), a bizarre colonial experiment took place on the rocky shores of Sydney’s ancient Indigenous harbour. Thousands of miles from home, England’s banished thieves were locked in a prison with ocean walls; forced to find food and cut through stone.

Defying the odds, their shanty camp survived and grew—clutching to life on the banks of a freshwater stream. Gardens were grown, goods were traded & rum soon ranked as both currency & cure.

As centuries changed, The Rocks was carved into cottages and corridors. Scallywags sailed into shore. Larrikins lurked in the laneways & many a clever convict swapped their chains for riches.

Journey Walks invites you to share a part in this remarkable story. This tour will keep your ears pricked, your eyes open and your passion for the past brought to life.

Your Guide:

This tour is led by local historians who specialises in storytelling and guiding groups through time and space. Expect history with a sense of humour and the kind of juicy detail that bring the past back to life.

The Walk:

While focussed on The Rocks district, your Journey Walk will include important relics and remains around Circular Quay such as those tucked away at Macquarie Place and hidden beneath the foreshore of Sydney’s original Cove— you will also venture inside Customs House to discover what’s hiding under its glass floor. In The Rocks, expect hidden cobblestone alleyways, charming sandstone ruins, historic pubs and heritage protected houses that make up Sydney’s most infamous historical quarter.

Your walking tour will cover:

  • Indigenous Sydney — the ancient harbour and its clans
  • Why did the convicts come? A clear context to transportation
  • The voyage, landing and struggles of the First Fleet
  • Secrets from the early convict colony
  • Convict craftsmen and entrepreneurs
  • The rum trade and its repercussions
  • Street gang stories and scandals
  • Sydney's oldest surviving cottage
  • Hidden sandstone structures and ruins
  • A visit inside Customs house and the Argyle stores
  • The remains of Sydney's slums and shanties
  • Models, maps and murals of new & old Sydney town
  • Any question you have answered in the spot

Suitability:

This tour is not recommended for children under 12 years of age as it involves adult content and ends at a pub in The Rocks.

While mostly on flat ground, several staircases are included in our walk due to the layout of The Rocks and thus the tour requires an ability to ascend and descend these flights. It is also important that guests are able to maintain their balance on cobbled surfaces, over grass and on sloped ground. Unfortunately these factors (especially the stairs) prevent easy access for those with strollers or wheelchairs — making the tour unsuitable for those with limited mobility.

A good level of English is recommended for this tour as the historic content will be brought to life through detailed stories and information (this is a talking tour just as much as a walking tour) and is currently not available in any other languages.

Adventure Tips

Wear sturdy, comfortable shoes

The route covers cobblestones and some stairs, so good footwear helps with stability and comfort.

Bring a water bottle

Stay hydrated during the 2.5-hour tour, especially in warmer months.

Arrive early for check-in

Meeting point is outside Customs House—arriving 5-10 minutes early ensures a timely start.

Not recommended for children under 12

The tour features adult-themed stories and a walking pace that may be challenging for young kids.

Local Insights

Wildlife

  • Harbor birds such as silver gulls and pied cormorants frequent the waterfront area.
  • Urban-adapted possums occasionally spotted in tree-lined laneways around The Rocks.

History

Sydney’s Rocks was Australia’s first European settlement, originally established as a penal colony in 1788, marking a complex chapter of colonial history that shaped the nation.

Conservation

Preservation efforts focus on maintaining the area's historic sandstone architecture and protecting archaeological relics while balancing urban development.

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Adventure Hotspots in Sydney

Frequently Asked Questions

Recommended Gear

Comfortable walking shoes

Essential

Protect your feet on uneven cobblestones and stairs throughout the tour.

Water bottle

Essential

Stay hydrated during your 2.5-hour outdoor experience.

summer|spring|fall specific

Sunscreen and hat

Essential

Protect yourself from sun exposure during daytime tours.

summer|spring specific

Light rain jacket or umbrella

Be prepared for occasional showers common in shoulder seasons.

spring|fall specific