20261023 Friday, October 23, 2026; Toledo and Flamenco Excursions
Our bodies are still getting adjusted to being on European time, waking at 5:30 a.m. instead of 3 a.m. We also discovered at breakfast that it is possible to order eggs and pancakes from the table, and Ben was able to get cappuccino instead of the awful drip coffee.
Today’s excursion to Toledo (pronounced To-Lay-do) was a very small group tour because half the extension group had booked a private train trip to Segovia instead of the optional Toledo tour offered by Viking. With only 6 guests, it was a very nice semi-private tour. We had the same mini bus for the hour-long drive southwest to Toledo.
Today was a bit of a history lesson on the Iberian Peninsula. Toledo was established around 200 BC by the Romans. The Visigoths took control in 400AD. Then the Muslims conquered in 700AD. The Crusaders then conquered in 1085. Toledo was the capital until King Philip II of Spain moved the capital to Madrid in 1561.
Toledo is called The City of Three Cultures because at times, it has been host to Muslim, Jewish, and Christian populations. It is nestled within a horseshoe bend of the Tagus River, which forms a moat around three sides of the city. A Roman and later Christian wall protects the fourth side of the city. It sits on a prominent hill, making it a natural fortress.
Our drive out to Toledo from Madrid was fairly unremarkable. Spain has modern and well-maintained highways, and the countryside between Madrid and Toledo is semi-arid agricultural land with olive groves interspersed with small suburban settlements and industrial areas.
Our tour of Toledo began with a drive around the perimeter of the city from around the Tagus River and the ancient city walls. The city spreads beyond the ancient walls into what is referred to as New Toledo. Within the ancient walls, the streets are narrow and radiate out from the top of the hill.
In years past, tourism in Toledo was a mess because of chaotic vehicular and pedestrian traffic in a congested small area. In the relatively recent past, changes were made to improve this situation. The city became a designated UNESCO World Heritage Site, and changes were made to restrict vehicular traffic within the ancient city walls. Now, only current residents and a limited number of taxis are allowed to drive within the city walls, with delivery vans and trucks restricted to limited hours of the day. A large parking complex was built outside the city walls with a series of escalators to take tourists up to the top of the hill and the center of the historic city.
Two ancient stone bridges cross the river like castle approaches. One is from the Moorish era, while the other “New” bridge was built by Christians about a thousand years ago.
After driving around the perimeter of the city, we made a stop at Toledo’s only remaining Damasus Steel Foundry. Toledo has been famous for the manufacture of swords with a technique that creates an extremely flexible and strong blade that excels in holding a sharp edge. Swords forged in Toledo were legendary throughout the Medieval and more modern world. The workshops still produce all manner of blades as well as jewelry which combines Damascus steel with intricate gold and silver inlays. This was also an important stop because the showroom has free bathrooms.
From the foundry, we were dropped off at the base of the escalators and ascended to the top of the hill and the heart of the ancient city after walking through and past some of the ancient Roman and Christian walls.
The city is like an ancient castle in many ways. There are hidden passageways and porticos among the spiderweb of cobble stoned streets. Our tour of the old city started at the Plaza de Zocodover, or Square of the Beasts of Burden. This name dates back to its origins as an Islamic livestock marketplace. In any other Spanish city, it would have been called the Plaza de Mayor.
Over the years, it has remained a central gathering point for the city. More recently, it has been jokingly referred to as McDonald’s Square because there is a McDonald’s and Burger King on the square. There are park benches all around the square decorated with tiles depicting scenes from Don Quixote.
There are also statues all over Toledo depicting Don Quixote. We even encountered the world’s tallest marzipan sculpture in the form of a larger-than-life-sized Don Quixote.
We strolled through the streets, gazing into shops offering marzipan, Iberian cheeses and ham, Toledo steel jewelry and edged tools, and countless restaurants and tourist shops. We happened to walk past the one place in Toledo where you can say “To-LEE-Doh” instead of “To-LAY-Doh”. That place was Calle de Toledo Ohio, named for its sister city of Toledo, Ohio.
We stopped at the Toledo Cathedral, which is an impressive Gothic cathedral and the seat of the Metropolitan Archdiocese of Toledo. Since 1088, it has held the highest rank over the entire Iberian Peninsula. It ranks higher than even the larger Catholic Cathedral in Madrid. David, our guide, joked that it was like a wedding ring in its box. While the box is bigger, the ring is more important.
The arrangement within the cathedral was interesting. There is a central Choir housing several organs and multiple rows of elaborately carved wooden seats, from which church officials would sing the entire mass. One technological feature was that although these seats folded down for sitting in, during a Mass, which could last several hours, attendees could only sit for very short periods of the ceremony. So when the seats were folded up, there was a tiny rest so that a “standing” person could actually rest their bottom leaning against the folded-up seat. The wood carvings were quite fanciful and included scenes of a woman in a shower and mermaids.
Opposite the Choir is the actual altar with a small seating area for dignitaries.
Peasants attending mass actually had to stand at the very back of the cathedral, behind the Choir in a location where you couldn’t even see the altar. TV monitors have been installed to allow peasants to see the altar in more modern times.
The City Hall of Toledo is across a small square from the entrance to the Cathedral. There is a “Fountain” of very modern origin in front of the City Hall which looks like a creekbed with water flowing through the center and bronze root-like structures radiating outwards in a linear trench.
Over the course of the day, the water level changes, but when the water level is low, trash and debris like gum wrappers and even dental picks and cigarette butts are trapped among the roots. Who knows just how long that “Fountain” will remain a part of that square.
Next, we wandered into the “Jewish Quarter” which is more a historical term than a demographic descriptor because since the 14th-16th centuries, Jewish people had been driven out of Toledo. Today, there is no active synagogue in Toledo, although since WWII, a small Jewish population has returned, although the main synagogue for them is in Madrid, so it’s a bit of a commute.
This led us to the Church of Santo Tomé, which contains one of the most important works by El Greco, “The Burial of the Count Orgaz”. Completed in 1586, it is considered one of his finest works, depicting the legend of St Stephen and St Augustine descending from heaven to inter the body of Count Orgaz, a major benefactor to the Church of Santo Tomé. His spirit, in the form of a ghostly infant, is directed between the terrestrial lower half of the painting and the gates of heaven above with Jesus, Mary, and John the Baptist preparing to receive his soul. Many characters make a cameo appearance in the painting, including many prominent nobles of the time, El Greco’s son, and El Greco himself, as well as Moses, Noah, David, and even Philip II of Spain, although he was still alive at that time. Philip II is depicted united with Christ in heaven.
Our next stop was the Santa Maria La Blanca, site of Toledo’s synagogue, which had been constructed around 1180 by Islamic architects for the Jewish community. Its architecture looks more like a mosque than a church with a simple and plain exterior and interior decorated with geometric and plant forms. Following anti-Jewish prgroms in 1391, it was converted to a Catholic church in the early 15th century. It is now a museum.
Our last stop was the Monastery of San Juan de los Reyes. One of the most interesting aspects of its architecture is the embedding of wrought-iron shackles into the exterior walls at impossible heights above street level.
These weren’t used during the Spanish Inquisition, but rather stand as a symbol of liberation of 15th-century Christian prisoners liberated during the War of Grenada. Once freed, captives or the Catholic Monarchs Ferdinand and Isabella brought the iron shackles to the Monastery as a public votive offering and sign of gratitude to God.
It was a pretty full day of pounding cobblestones through the ancient city, so it was a quiet ride back into Madrid. After a short nap, we loaded back up into the mini-bus with 3 other couples for a dinner and Flamenco evening at the Corral de La Moreria. This was an intimate affair in a small venue with a Michelin Star.
The dinner was fancy, starting with Scallop Carpaccio with Tomato Tartare, Dates, and Coconut Garlic. The main was something called Mellow Beef, sautéed Boletus, and Mashed Potatoes, and dessert was Five Textures of Chocolate. Dinner was served with wine and followed by a glass of Sherry as the Flamenco show began.
The show was performed by a cast of 5 musicians and two dancers. The stage was in a corner of the small venue, but there were pillars that obscured parts of the performance, and we happened to be seated about as far from the stage and with many pillars between us and the stage as you could get.
But the performance was energetic, emotional, and passionate. The dancers did work their way through the audience to the stage, so we did get a really close look at their performances, at least briefly. The wine was also pretty free-flowing throughout the evening. This was a pretty memorable way to wind up our visit to Madrid.
Tomorrow morning, we fly out of Madrid and check into a hotel in Lisbon for the next stage of our trip.


























































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