The building to the left is the Alcazar which houses the Army Museum today.
Toledo is a great day trip from Madrid but I would recommend staying overnight to enjoy the city at night. It is easy to catch the train from the Atocha train station. The high-speed AVE train makes it a quick 30 minute trip from Madrid to Toledo. There are approximately 8 trains that leave every 2 1/2 hours throughout the day. I would recommend getting your tickets the day before as the early train to Toledo and the last train back to Madrid sell out quickly.
I visited Toledo back in 1984 and just loved the city then. Not much has changed except there were more tourist and the addition of escalators to take you up the steep hill to the center of the city. One of my fondest memories of my first trip to Toledo is sharing it with my brother, Perry and the picnic we shared on the ancient wall that surrounds the city. We had the typical bread, cheese, fruit and wine. I remember the wine cost 30 cents and when we returned the bottle, we got 15 cents back!!! It wasn’t the best wine but when you are on a tight budget, like we were, it was a great deal!
It was wonderful to return to Toledo and to share it with David. 34 years later, it was the same town but offering more souvenir shops and more people were walking the narrow, quaint streets. If I had it to do over again, I would go to spend at least 1 night there. I remember from my first visit how beautiful it was with the cathedral lit at night as well as the bridges and streets.
The artist, El Greco, spent the last 37 years of his life in Toledo. There is a museum dedicated to El Greco’s art and the Santo Tomé chapel displays one of his most popular painting among his admirers….The Burial of the Count of Orgaz. It was placed in this church by El Greco 400 years ago!
David and I didn’t visit any of the museums in Toledo, we mostly walked around absorbing the beauty of this city on the hill. 
Toledo has a rich history with three cultures coexisting – the Jewish, the Christians and the Muslims. Upon arriving at the Toledo train station, you immediately see the Moor’s influence with the neo-Moorish architecture.
The lobby of the train station.
Walking through Toledo, there were reminders of Moor’s rule. This Moorish influence tower is the entrance to the University of Castilla-La Mancha University.
Cambron Gate is one of many gates on the wall of Toledo. This gate, located in the west part of Toledo, was also known as the “gate of the Jews” was the main entrance/exit for the Jewish quarter of Toledo. In 1576, this current Renaissance-style structure was built.
A short walk from Cambrón Gate is San Martin’s Bridge which crosses over the Tajo River. It was built in the 14th century. It was fortified with impressive gates at each entrance.
One of the gates to the San Martin Bridge with the Monastery of San Juan de los Reyes in the background.
Looking from the bridge up the Tajo River.
For the thrill seeker, there is a zip-line company near the bridge.
This is part of the ancient wall that was built around Toledo by the Romans during the 1st Century. When the Arabs took control of Toledo in 711 AD, they developed the city more and widen the city wall. After the Reconquista in 1492, when the Christians took control of Toledo, the walls were expanded and new gates were built. They remain the same today from that last reconstruction.
A view from the wall.
Some of the narrow streets of Toledo. Within the city walls, it is a “car-free” zone except for the residence’s vehicles.
Not a narrow street but found along one of the streets. This is one of my favorite pictures I took while in Toledo. I love the different textures and simplicity of it!
Walking through the streets, you can suddenly come into one of the many open plazas:
The red and yellow banners in this plaza is a show of Spanish patriotism that has been spurred by the Catalan’s drive for independence from Spain back in October 2017.
The Toledo Cathedral is said to be one of the best in Europe. After the Reconquista, when the Catholics took control of Spain, this cathedral was built where a mosque once stood. We didn’t go in but I know I visited it 34 years ago before they started charging 10 euro to see the inside!
The Last Supper over the main entrance of the Toledo Cathedral.
When in Toledo, you should splurge on their famous sweet – marzipan! The nuns of Toledo used to be the main producers but with their numbers shrinking, there are other ways to enjoy this Toledo delicacy. There are stores throughout the city that offer marzipan goodies. We tested cookies that were stuffed with chocolate, caramel and strawberries….all very, very sweet! We also enjoyed a piece of candy made from this almond-flavored sweet!
I really think that if planning a trip to Madrid, you need to plan for a day and night in this wonderful walled city of Toledo!