Madrid Diary Day 5: Toledo, City of Three Cultures

Madrid, Spain – Wednesday, October 16, 2019 – PART ONE

[Find this travel series here]

Today we traveled back in time! But, we almost missed the adventure before it began. This morning we leisurely walked to the designated meeting place for our bus [the Starbucks in Plaza del Callao]. But, it felt disconcerting there was no one else waiting for the bus. By 9:10 we ran across the street to the hotel where we had purchased the tour. We were told our pick-up was actually at 8:10!! OH NO!!!😮 The concierge reassured us there was still hope. If we hurried and took a taxi we might be able to catch up to the bus since it was collecting people throughout the city. I quickly flagged a Taxi, and our driver navigated the busy morning traffic like a boss! He got us to the tour office in record time, and our bus was waiting across the street! Crises averted! (Whew)


One-hour by bus south of Madrid brings you to Toledo, the stunning “City of Three Cultures” built literally on top of a giant hill of rock, surrounded by the powerful Tagus River, which serves as an imposing natural moat. During our time here, I was struck over and over how much this historic city reminds me of Jerusalem in its history, physicality, and spirit. From its many different temples, shrines, and mosques, to its narrow cobblestone passageways. This ancient walled fortress traces its roots to 200 BC and beyond. It is considered a sacred site and pilgrimage for three cultures – Christians, Jews, and Muslims.

Fun Fact: This is the origin of the expression “Holy Toledo!”

The earliest records speak of this city as a Celtic fortress. Toledo was conquered by the Romans who made it their stronghold during the time of Christ.

Toledo is a World Unesco Heritage Site, and it has been preserved beautifully. To protect the authenticity and integrity of the city as much as possible no large roads have ever been built within the city walls to accommodate tour buses or taxis. However, local authorities found a creative solution that allows tourists to reach the city safely and still preserve the integrity of the site via a series of escalators built into the side of the rocky mountain, artistically concealed – transporting us up -up – up to the top.

Can you spy the escalator?

Toledo has always been considered the holiest site in Spain. Each time this city was conquered, it was treated as sacred ground which helped to preserve it from destruction and vandalism. Because of this, walking up and down these winding narrow cobbled alleyways truly transports visitors back in time. This city has been ruled and inhabited by Celts, Moors, Visigoths, Romans, Arabs, Jews, and Christians. It seems every corner has another cathedral, church, chapel, temple, or mosque. For many centuries the Christians, Jews, and Muslims all lived peacefully together here in their separate quarters of their “City of Three Cultures”. Sadly, their harmony would not last. The Sephardic Jews were persecuted, massacred, and driven out. The Muslims also faced a similar fate.

Our bilingual guide was terrified he would lose our group, so every few minutes he would warn us through our headsets that if we did not “please sticky together” we may become lost forever in the labyrinth of the city! 🙂 We soon learned he was not exaggerating!


We got to see a famous original painting by El Greco on the wall of a 12th Century cathedral, Iglesia de Santo Tomé. Our guide explained the symbolism of this unique huge wall painting which took the artist three full years to complete (1583 – 1586). The commission depicts “The Burial of Count Orgaz” – a wealthy donor beloved by the people. In the painting, we see the body of Count Orgaz being laid to rest in the ground, while the bright soul of the Count travels upward into the clouds – at the feet of the Mother Mary an angel helps the soul squeeze through the clouds shaped like a “birth canal”. Then, we see the freshly “reborn” Count worshiping at the feet of Christ, joined by the apostles and many other Saints. It paints an epic concept of death as a literal rebirth. There are a lot of other cool things about this painting (to learn more, go here). El Greco was truly ahead of his time!

The Burial of Count Orgaz – by El Greco (1586) –  Santo Tomé, Toledo

Toledo has been a leader in sword-making and steel workmanship since 500 BC! Its reputation for the best swords and weaponry in the world contributed to making Toledo a very desirable conquest! We visited a traditional craftsman factory to see how steel swords and other gold and silver crafts are created.

Everything was very beautiful! And also very expensive. So, we took photos for our souvenirs.

We exited the city by walking across the Puente de San Martín – a gorgeous Medieval bridge constructed in the 14th Century that spans the mighty Tagus – the longest river in the Iberian Peninsula!

Enjoy This Toledo Video I made just for you!

Tune in for PART TWO of this exciting day when we visit historic SEGOVIA.

Adios, Holly


  1. I have really enjoyed this series. I get to travel the world through you. Love the video. I had a minor in Art History and seeing that painting was a treat. I can’t imagine taking 3 years to paint a picture, but when you see all the detail, you understand. Looking forward to part 2. Love you, Lynne

    Liked by 1 person

I love your comments! ♥

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s