Philadelphia Tours and Experiences See what others overlook. Understand what others don't.
Colonial history meets an authentic urban vibe in Philadelphia, a former Quaker enclave that grew into the most important city in Colonial America.
Philadelphia Private Walking Tours
Context Travel Philadelphia Tours
Philadelphia, a city steeped in history, is renowned for its pivotal role in the founding of the United States, hosting the signing of the Declaration of Independence and the Constitution. Its streets echo with the legacy of figures like Benjamin Franklin, William Penn, and the birth of American democracy. This rich historical backdrop sets the stage for Context's Philadelphia tours, where scholars and historians reveal the city's multifaceted past. Notably, Context Travel's headquarters is based right here in Philadelphia, providing a unique local perspective on the city's history.
Our flagship Philadelphia walking tour is our Philadelphia Colonial History Tour. This tour begins by exploring the city's layout and the visionary influence of William Penn, who not only founded Pennsylvania but also designed Philadelphia's grid system. Starting near the plaza-scale plan by Second Street, we'll see how Penn's design fostered commerce, trade, and immigration. As we traverse the historic core, we'll examine themes like Quakerism, religious tolerance, and open trade highlighted by buildings over 200 years old.
Depending on availability, we might visit historic homes, museums, and significant churches like Carpenter's Hall, Old St. Mary's, St. Peter's, and Independence Hall. Our narrative will cover Philadelphia's evolution through the colonial period, focusing on the rise of a wealthy merchant class and their impact on the city's social, architectural, and political landscape up to the American Revolution.
We conclude our tour at Headhouse Market in Society Hill, once a bustling trade center, now a lively farmer's market, providing a fitting end to our journey through Philadelphia's colonial history and its key sites in Old City.
By choosing Context for your Philadelphia tour, you're opting for an experience that goes beyond conventional tourism. You're stepping into a narrative crafted by those who live and breathe history, offering you a Philadelphia private walking tour that's both educational and profoundly engaging.
What Context Philadelphia Travelers Say
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158 Reviews
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It was such a pleasure to spend the afternoon with John!
We learned so much about Philadelphia and Pennsylvania - information that was both new and fascinating. Even my aunt and uncle, who are longtime locals, were so impressed.
John struck a wonderful balance of being inclusive, incredibly knowledgeable, and easy to talk to. He made the information not only understandable, but also deeply relevant. It felt like we could ask about anything, and he’d be able to tie it back in a meaningful way. He was clearly a valued member of the local community - he seemed to know everyone at our stops, and they knew him.
What stood out most was the way he highlighted the distinction of Pennsylvania and Philadelphia’s own history within the broader story of America. It’s incredibly fascinating - and something I now want to dive deeper into.
It left me walking away with a new sense of pride for the city and for the state.
Thank you again - it was a very special experience.
Hyo
Jun 29, 2025
Joella was so knowledgeable and helpful, we throroughly enjoyed our tour.
Pamela
Jun 2, 2025
Our guide Charlene was very nice, knowledgeable, and accommodating. Had a wonderful time and really enjoyed the content of the tour!!!
Daniel
Apr 20, 2025