Sydney Private Walking Tours

Sydney Tours and Experiences See what others overlook. Understand what others don't.

A former 19th-century hardscrabble penal settlement evolves into a 21st-century world-class city.

Sydney Private Walking Tours

Context Travel Sydney Tours

Sydney, born from the arrival of the First Fleet in 1788, has evolved from a penal colony into a bustling metropolis, its streets layered with the stories of convicts, immigrants, and the trials of history. For those curious about this transformation, our Sydney walking tours offer a window into the city's past. 

Our Introduction to Sydney Tour is a comprehensive exploration of Sydney's history. This tour, led by local historians who bring depth and insight to every narration, covers the spectrum from the initial British settlement to the cosmopolitan city we see today. You'll gain an understanding of how Sydney's landscape and society have shaped each other through the help of a passionate local expert.

For those intrigued by the gritty details of Sydney's social fabric, our Rocks History Tour delves deep into the lives of the city's early inhabitants. This private tour uncovers the stories of convicts, the impact of immigrant groups, and the dramatic episodes of labor unrest and the bubonic plague. Walking through The Rocks, you'll learn about the resilience and spirit of Sydney's people, guided by experts who illuminate the past with a passion for storytelling.

Both tours provide an intimate, immersive experience where you can engage directly with Sydney's history. Join us to uncover the layers of history beneath Sydney's modern facade, guided by those who know it best.
What Context Sydney Travelers Say
(4.85) 163 Reviews

Reviews can only be left by Context customers after they have completed a tour. For more information about our reviews, please see our FAQ.

Matt was an excellent guide for our interest in history and city planning. We saw many important sights within Sydney CBD and learned so much about the city's development. Just as importantly, he was a lot of fun to tour the city with!
Mark was wonderful but the weather didn’t cooperate so we had to pivot from our original plan. Mark had amazing breadth of knowledge and history and loved the tour!
Mark provided a comprehensive and entertaining overview of Sydney’s history and attractions. We highly recommend Mark’s tour as an introduction. He even suggested activities for our next two days as well as restaurant recommendations!
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