A Short Visit to the Historic Streets of Toledo

Toledo is a small old city about an hour’s drive south of Madrid. Because our hotel was in the center of town, we got a small tour while driving around trying to find the hotel.

Driving into Town and a Helpful Parking Lesson

We met up with some other digital nomads recently and I mentioned that we’ve really learned a lot about travel logistics over the years. They wanted to know what exactly we had learned, and our arrival in Toledo turned out to be a perfect example.

We stayed right in the historic old town, which almost always means an absolute headache for driving and parking. Because of that, I researched exactly where to park well before we arrived. I had the name of a garage handy, and we spied it right where the map indicated as we approached the town center. We immediately pulled in, and I figured out that the hotel was just a short walk away. We decided to park right then and drag our bags over the cobbles. If we hadn’t done this, we might have dropped the luggage off a tiny bit closer to the entrance. However, Mike would have had to drive all the way back around those winding, one-way streets just to return to that exact same garage. It is just a bit of hard-earned knowledge that saved us a lot of time.

Our Stay at the Eugenia de Montijo

There are quite a few hotels to choose from in town, and we picked one from the Marriott collection called the Eugenia de Montijo. It claims a five-star rating, but in my mind, it didn’t really live up to that reality. The service itself was perfectly good and the location was great, right in the heart of the town. My big beef was that the internet ran incredibly slow the entire time we were there. For the last half of our stay, it just stopped working altogether.

I went down to the front desk to ask about it, and they just shrugged. “Yeah, well, it’s the weekend,” they told me. “We probably won’t be able to fix it for a few days.” Frankly, if you want to call yourself a five-star hotel today, you simply have to provide decent, working internet. It wasn’t great to begin with, and going down completely made things rather tricky for us. While it is a nice enough place in a great location, I certainly wouldn’t go back. The fact that they allowed their internet to remain so poor, let alone broken for days, just indicates where their priorities sit. If you are happy to visit completely disconnected from the digital world, then it is fine. Otherwise, you might want to look elsewhere.

Exploring the City of Three Cultures

We had originally planned a day trip out to Cuenca. However, after our big days exploring Segovia and El Escorial, we decided Toledo had more than enough to fill our remaining two days. As we so often do, we arranged a local walking tour on our first morning. This gave us a wonderful introduction to the town and pointed out the places we should visit later on our own.

The old town of Toledo is incredibly compact, full of narrow streets that measure just a few feet wide. We noticed the locals use specially adapted little trucks just to deliver goods through the tight gaps. The city has a fascinating history. People call it the “City of Three Cultures” because Christian, Muslim, and Jewish communities lived together here peacefully for centuries. It served as a Roman outpost, a Visigothic capital, and a major Moorish stronghold over the years before becoming the heart of Castile. During our walking tour, we learned that Toledo became a very wealthy town. At one point, the king’s business manager was actually a Jewish man from right here in the city.

The Massive Toledo Cathedral

The central building in the entire old town is the Cathedral, officially known as the Primate Cathedral of Saint Mary of Toledo, and it is absolutely huge. Workers started building this High Gothic structure all the way back in 1226 under King Ferdinand III. The site previously held a sixth-century Visigothic church and a Moorish grand mosque, and builders didn’t actually finish the cathedral until 1493.

Inside, you find an enormous central choir area, a significant number of historic tombs, and two magnificent organs. The famous altarpiece features more than twenty detailed paintings. It was also wonderful to see incredible original paintings by El Greco, Goya, and Titian tucked away in various chapels. What a treat.

The Beautiful Monastery of San Juan de los Reyes

Another highlight of our time in town was the Monastery of San Juan de los Reyes, which ranks as one of the most beautiful Gothic temples in Spain. King Ferdinand II of Aragon and Queen Isabella I of Castile founded the monastery to celebrate the birth of their son, Prince John. They also wanted to commemorate their victory over the Portuguese army at the Battle of Toro back in 1476.

The monarchs originally chose the building for their final burial place, though plans changed later and they ultimately chose the Royal Chapel down in Granada. Dedicated to Saint John the Evangelist, workers constructed the building between 1477 and 1504. Today, it still functions as a working church. The two-story cloister is truly one of the most magnificent ones I have ever seen. It features abundant green vegetation and gorgeous, intricate coffered ceilings that make you feel as if you’ve stepped right into a quiet paradise. They encourage visitors to wander through, and you can see several famous original paintings by El Greco hanging inside the monastery walls.

Walking Through Jewish History

Like many other historic towns across Spain, Toledo’s old Jewish quarter is clearly marked along the paths by small metal and ceramic tiles embedded in the ground. There are two major synagogues here that are currently open to the public, and they have incredibly layered histories.

The first is a simple white synagogue, often called Santa María la Blanca. It is little more than a single room, but the historic plaster work still clinging to the walls and ceiling is absolutely impressive. After the Jews were expelled from Spain, the chapel was turned into a church, which was a common theme here. In fact, some of these buildings even served as mosques at various points in their long histories. The second synagogue houses the Sephardic Museum, and it is a beautiful testament to the city’s mixed past, featuring both Arabic script and Hebrew script woven side-by-side into the decorative plaster work. Like the first, this one also became a Christian church after the Jewish community was forced to leave.

Partridge, Pork Stew, and Local Marzipan

While there is a lot of excellent local food available, the real name of the game in Toledo is marzipan. It is absolutely everywhere you look, it is completely wonderful, and shops offer an endless variety of different treats made with it. You should definitely check a local bakery out if you visit.

There are also a number of Michelin-rated restaurants tucked into the winding alleys, so of course we had to treat ourselves and try a few. The first was Splendio Trattoria and then La Cabala.

We noticed a few distinct dishes appearing on almost every menu around town. The first is local partridge, which seems just a little bit bigger than a Cornish game hen. Chefs frequently stew it or serve it up with rich sauces. I ordered it one night and it tasted really quite good, so I definitely recommend checking that out. Two other traditional dishes are also well worth looking into. First, you have Carcamusas, which is a delicious, slow-cooked pork stew. The second is a hearty venison stew, which you will spot on most traditional menus around town. They make perfect, comforting meals after a long day of walking.

Don Quixote and Tilting at Windmills

Toledo shares a close history with the story of Don Quixote, and you will see references to him all over town. Miguel de Cervantes, the author, lived here for a period of time, which explains why the area relates so deeply to his writing. Critics frequently consider Don Quixote to be the very first European novel. There were certainly other stories at the time. This book was the significant one that influenced so much of modern literature.

On our way out of town, we stopped in a small village about an hour away from Toledo. It sits along the Ruta de Don Quijote. A driving route that highlights various spots the character visited in the book. This particular town features an old castle and six or seven historic windmills lined up along the top of a high ridge.

These windmills look quite a bit different than the ones we see in Holland. Because the dry region lacked flowing river water, the locals couldn’t rely on watermills to grind their grain. They could only use donkeys or harness the wind. As a result, they built these round white mills up on the highest hill to catch the best breeze. Of the five mills standing there today, two or three still hold their actual internal grinding machinery. One of them still works fully and functions as a live demonstration for tourists. It was really neat walking among these old structures, checking out the giant sails, and learning a bit more about how they worked.

Summer Finally Arrives

The weather finally warmed up for us by the time we reached Toledo. The cold, damp days and chilly nights that we experienced back in Barcelona, and then a bit more in Madrid, have finally passed.

We are now solidly into the beautiful beginning of summer. Having daytime temperatures up in the 80s made for some really pleasant days of exploring the sunny streets of Toledo, and the warmth has definitely changed our moods for the better. Not a bad way to travel at all.

Have you ever visited Toledo, or perhaps followed the trail of Don Quixote out to the old windmills?