The origin of the phrase “Holy Toledo” is a hotly contested topic. However, at least one origin story traces its roots back to the Holy Kingdom of Toledo in Spain. This is a hill town in central Spain with a curious religious history. We recently took a walking tour of the Toledo attractions to understand what makes this place so unique.
My interest in this city started some 25 years before. As a high school student, friends of my parents had visited Toledo and brought back incredible photos of a hill-top town with stunning architecture. I was in my geeky architecture phase, and loved the photos.
On our first trip to Spain in 2008, I’d wanted to visit Toledo but we couldn’t fit it into our already jam-packed trip. I knew we’d be back.
A recent trip to Madrid brought us back and my goal of visiting the Toledo attractions of churches, mosques and synagogues would be realized! To make the most of our time at this UNESCO World Heritage Site and learn the most possible, I booked us into a Context Travel walking tour of Toledo. Truthfully, a walking tour is one of the single best things to do in Toledo to understand this complex and unique city.
For hundreds of years, this city has been a center of culture, religion and education since the medieval times. In this city, Christians and Jews lived in peaceful coexistence with Muslims and under Islamic rule. For this reason, it is known as the “melting pot of three cultures.”
The center of life today is the Cathedral. This magnificent building from the seventh and eighth centuries features cavernous spaces, intimate alcoves, Gothic alters and spectacular religious painting by the Spanish Enlightenment master Francisco de Goya. As in the similar cathedral not far away in Segovia, it would be easy to spend an entire day exploring this incredible Cathedral, but there are other Toledo attractions to explore.
Toledo’s Jewish history is really Spanish Jewish history. It’s one of tolerance, confusion and troubles. These themes played themselves out at the Synagogue of Santa Maria la Blanca (the white synagogue), which is widely believed to be the oldest synagogue still standing in Europe (but now owned by the Catholic Church). Visitors will immediately recognize the strong Moorish architectural style, which is for good reason: it was built by Islamic architects for a Jewish congregation.
Spain’s Jewish heritage is on full display at the Museum of the Sephardic Culture, housed in a 14th century synagogue. While museum effectively documents Jewish life in Spain, it is most interesting in viewing the larger context of how Judaism influenced modern Spanish culture.
Despite the story of a peaceful coexistence in the city, the city saw more than its share of war and destruction. The Spanish Inquisition brought that peaceful coexistence to a close with the expulsion of Muslims and Jews. Napoleon brought his own unique blend of governance to the Iberian Peninsula. And the wars of the 20th century didn’t leave Toledo unscathed.
It is perhaps both ironic and fitting that the Spanish National Military Museum (Museo del Ejercito) is located in Toledo. While we’re not much for military stuff, the museum was interesting and houses an impressive section of the original town fortifications. Our Context Travel Toledo walking tour covered the museum, but not every tour visits the museum (note that all Context Travel walks are custom-tailored to the group).
For us, visiting Toledo was the fulfillment of a decade-long dream. There is truly no better way for us to explore the numerous Toledo attractions than on a Context Travel walking tour. As we left town, we found ourselves muttering that common phrase: “Holy Toledo!”
“There was a discordant hum of human voices! There was a loud blast as of many trumpets! There was a harsh grating as of a thousand thunders! The fiery walls rushed back! An outstretched arm caught my own as I fell, fainting, into the abyss. It was that of General Lasalle. The French army had entered Toledo. The Inquisition was in the hands of its enemies.”
― Edgar Allan Poe, from “The Pit and the Pendulum“
Lance Longwell is a travel writer and photographer who has published Travel Addicts since 2008, making it one of the oldest travel blogs. He is a life-long traveler, having visited all 50 of the United States by the time he graduated high school. Lance has continued his adventures by visiting 70 countries on 5 continents – all in search of the world’s perfect sausage. He’s a passionate foodie and enjoys hot springs and cultural oddities. When he’s not traveling (or writing about travel), you’ll find him photographing his hometown of Philadelphia.