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A Holy Toledo Walking Tour

The best way to see the Toledo attractions is on a walking tour.

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. Toledo 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.

The old city of Toledo, Spain is recognized as a UNESCO World Heritage Site.

My interest in Toledo, Spain 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.

There are so many great things to do in Toledo, Spain.  Around every corner is a beautiful scene begging to be photographed.

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.

A view of Toledo's Cathedral down one of the many lanes in the old town.

For hundreds of years, Toledo 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, Toledo is known as the “melting pot of three cultures.”

The exterior of the beautiful cathedral - one of the top Toledo attractions.

The center of Toledo 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. It would be easy to spend an entire day exploring this incredible Cathedral, but there are other Toledo attractions to explore.

The ceiling of the impressive Cathedral of Toledo.

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.

One of the top Toledo attractions is the Synagogue of Santa Maria la Blanca (the white synagogue) with its distinctly Islamic/Moorish architectural style.

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.

The synagogue that is the Museum of the Sephardic Culture in Toledo, Spain.

Despite the story of a peaceful coexistence in Toledo, 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.

Part of the original Toledo fortifications inside the Spanish National Military Museum (Museo del Ejercito).

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).

Details inside the Synagogue of Santa Maria la Blanca, one of our favorite sites in Toledo.

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!”

The local convent in Toledo sells these delicious (and holy) cookies.  Eating one of the convent cookies is one of the top things to experience in Toledo.

The local convent in Toledo sells these delicious (and holy) cookies

We were the guests of Context Travel on their Toledo walking tour. As always, all opinions of the historical and thought provoking are our own.


“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”






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What do you think about A Holy Toledo Walking Tour?

  1. Tania January 10, 2017 at 9:53 am #

    Love this write-up. The buildings are so beautiful. It’s no wonder you fell for it during your ‘geek’ architecture phase!
    Tania recently posted…ForwardMy Profile

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