Cape Town Tours and Experiences See what others overlook. Understand what others don't.
Nicknamed "Mother City," Cape Town is the de facto heart of South Africa.
Cape Town Private Tours
Context Travel Cape Town Tours
Cape Town, nestled between the Atlantic Ocean and the iconic Table Mountain, is a city where every corner tells a story, where history and culture are not just learned but experienced. Our private Cape Town walking tours are your key to unlocking this rich heritage, led by knowledgeable Cape Town tour guides who bring the city to life in ways guidebooks never could.
Introduction to Cape Town Tour: Dutch Trading to Democracy - Start your exploration with a comprehensive Cape Town walking tour that traces the city's evolution from its inception as a Dutch trading post in the 17th century to its vibrant democratic present. This tour includes a visit to the formidable Castle of Good Hope, where layers of colonial history unfold, and a stroll through the city's diverse neighborhoods, offering a glimpse into its multifaceted identity. It’s the perfect Cape Town tour for those seeking to understand the foundational stories that have shaped this "Mother City".
Bo-Kaap Neighborhood Tour: Immigration and Islam - Delve deeper into Cape Town's cultural mosaic with our private Cape Town tour focused on the Bo-Kaap, where the vibrant hues of the houses are as colorful as the history they represent. Here, Cape Town tour guides will guide you through the stories of the Cape Malay community, exploring themes of immigration, Islam, and the enduring spirit of a people whose resilience is as bright as their homes. This Cape Town walking tour not only educates but also celebrates the cultural amalgamation that defines this unique enclave.
Simon's Town History Tour - For those fascinated by maritime tales and lesser-known historical narratives, our Simon's Town History Tour offers an in-depth journey. This private Cape Town tour takes you south to Simon's Town, where the sea whispers tales of naval exploits, slavery, and the silenced voices of history. Your Cape Town tour guide will navigate you through this historic town, uncovering its role in the British Empire's naval strategy, its connection to the liberation struggle, and the poignant stories of the individuals who lived here.
Each of these Cape Town tours lasts approximately 3 hours, designed for those who wish to experience the city beyond the surface. Whether you're a history buff, a culture enthusiast, or simply looking to orient yourself upon arrival, our walks provide a deep dive into what makes Cape Town truly special. From savoring local delicacies like biltong and fynbos tea to exploring wine routes in Stellenbosch and Franschhoek, every tour is crafted to enrich your understanding and appreciation of this stunning city.
What Context Cape Town Travelers Say
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54 Reviews
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Our guide was informed gracious and spry. We had a most interesting and fun tour.
Marlene
Mar 13, 2025
We had a terrific morning with Lesley, on our Introduction to Cape Town tour. She was clearly knowledgeable and created a connection with me and my family that exceeded my expectations. In addition the broad swath of Cape Town and South African history, she also provided a nuanced perspective that highlighted the ongoing challenges of addressing the realities of colonialism, Apartheid, and exclusion that have been part of this beautiful countries past. She also went above and beyond, by giving us suggestions on art and music happenings as well opportunities for some limited sporting events. I would highly recommend this tour and her leadership!
Ben Olk
February 17, 2025
Ben
Feb 26, 2025
I had seen most of the sites Joline showed via a self-service tour. Joline provided such greater depth and knowledge that I felt I was attending for the first time. Her knowledge of the history and personal perspective was only exceeded by the warmth of her personality and humanity. She is an excellent guide with a beautiful spirit. I was enriched by the tour but I am a better person after meeting her.
Edwin
Oct 23, 2024