Toledo: UNESCO World Heritage Site, Imperial City, City of Three Cultures, Old Capital of Spain, Current Capital of Castilla-La Mancha, and former home of famous painter El Greco. That’s a lot to be known for!
A few hundred years ago, Toledo was the capital of Spain and Madrid was just a small village. Toledo was called the Imperial City because it was where Holy Roman Emperor Charles V held his court until 1556. In 1561, Charles V’s son, King Philip II, moved the capital to Madrid, and the court went with it. It still serves as the capital of the Castilla-La Mancha community in central Spain.
Toledo is also known as the City of Three Cultures because there is a heavy influence from Muslim, Christian, and Jewish cultures. Many of the old mosques have been converted to churches, or serve as both mosque and church. There is still a Jewish quarter in Toledo to this day, where you can see medieval synagogues, some of which have also been converted into churches.
Finally, El Greco (translating literally to “The Greek”) was a Greek painter, sculptor, and architect of the Spanish Renaissance. At 36 years old, he moved to Toledo where he lived and worked until his death at 73 years old. In Toledo, El Greco produced some of his most well-known paintings, which you can see in the El Greco museum and Primate Cathedral of Saint Mary of Toledo.
What to See in Toledo
Being only 30 minutes by high speed train, Toledo is a popular day trip from Madrid, but to really get the feel for this medieval city, try to book a few days. If you do decide you only want to go for a day, book your train tickets in advance; they sell out!
Catedral Primada de Toledo (Primate Cathedral of Toledo)
The main cathedral in Toledo is hard to miss. The Primate Cathedral of Toledo is the second largest cathedral in all of Spain, following closely behind Sevilla‘s cathedral.
Toledo’s cathedral has the third largest bell in the world, weighing 18,000 kg (almost 40,000 pounds or 20 tons)! It was so big that it only rang once, in the 18th century, and the sound was too loud and cracked the bronze material of the bell. The two bells in the world that are bigger, in Germany and Russia, had the same problem. Now, the bell is just for show. Not to worry, you can hear bells from other churches in the city ringing every hour.
Toledo’s Primate Cathedral had a problem of sinking into itself. Toledo is surrounded on three sides by the Tagus River. The humidity underground caused the cathedral’s smaller tower to crumble. To remedy this, the architects needed to create two arches to keep both towers up. You can see the arches inside.
Don’t miss the art museum inside the cathedral, where you can find paintings and sculptures by artists like El Greco, Rafael, Francisco de Goya, and Michelangelo.
Also inside the cathedral is the treasury, where you can see 500-pound, 10-foot high gilded Monstrance. Every year during Corpus Christi, the Monstrance was carried by men through the hilly, windy, narrow streets of Toledo. Luckily, there are now cranes to carry this heavy gold piece through the streets during the Feast. See more in depth about the cathedral’s treasure in this After Orange County blog post.
The cost to enter the cathedral is 10€. You get a headphone set to help navigate the beautiful chapels, museum, and treasure room. Alternatively, you can book entrance with a guide with the City Sightseeing Bus for 15€.
Right outside the cathedral is Cathedral Plaza, also known as the Square of the Three Powers. On one side, you have the cathedral. Across from the cathedral, you have the Palace of the Archbishop. On another side you have City Hall, which also houses a tourist information center on the bottom floor. Finally, in the corner between City Hall and the cathedral is the police station. So there you have it: justice, religious, political. The three powers!
Plaza Zocodover and the Alcázar
Plaza Zocodover sounds intimidating to say if you’re asking someone where to find it. It’s pronounced: THOcodoBER (in the Spanish accent). It’s the hotspot and central meeting area for all things in Toledo. If you’re staying in Toledo, this is the central area you’ll want to be in if you want to stay close to the action.
Plaza Zocodover is also where you’ll find all of the walking tours, tourist train, City Sightseeing Bus, souvenir shops, and touristy restaurants. I recommend all of these things (except maybe the touristy restaurants).
Definitely join a free walking tour. Most of the tours are in Spanish, but tour guide Maria hosts an English version every day at 11:00 am. She does an amazing job! Unfortunately those are the only two languages the tours are currently offered in (as of 2019), but hopefully visitors speak either English or Spanish.
The free walking tours give you a lot of history and cover a lot of ground, so wear comfortable shoes. The guided tours turn what feels like a big mysterious city that’s easy to get lost in into a small medieval village that you can easily find your way out of. After all, Toledo isn’t really that big.
I also recommend the City Sightseeing Bus. The bus costs 15€ and takes you around the outside of Toledo for some excellent shots of the city from afar. The bus ticket is valid for 24 hours, and I highly recommend doing the route twice: once during the day and once at sunset for some gorgeous night time photos of Toledo all lit up! For an added fee, you can take a walking tour of the historic city or a guided tour of the cathedral.
Finally, the Alcázar is an old Roman palace from the 3rd century. It’s a stone fortress and the highest point in Toledo. It’s impressive to view, but I couldn’t find a way inside. There is a museum on one side and a library on the other side. The library is worth a visit, but surprisingly not for the books. Take the elevator to the top (for free!) where you can visit the cafe, have a beer (in the library), and take selfies of the incredible views above the city!
Mezquita del Cristo de la Luz (Mosque of Christ of the Light)
This special mosque has a pretty awesome story behind it. Dating back to 999 AD, it’s the only surviving mosque of the ten that once stood around Toledo, making the Moorish architecture of stone mixed with brick unique. It’s also unique in that it faces Córdoba, not Mecca like most mosques.
Legend has it that King Alfonso VI of Spain rode down the Road of the Romans (which you can still see part of in front of the mosque), when his horse came to a stop in front of the mosque and knelt down on one of the cobblestones. According to the tale, the horse looked inside the mosque and saw a light illuminating the mosque. King Alfonso entered the mosque and found a vision of Christ. He immediately converted the mosque into a chapel and named it Christ of the Light. The cobblestone where his horse knelt outside the mosque is white.
Calle Alfileritos (Pins Street)
If you find yourself in Plaza San Nicolas, venture down the narrow Alfileritos Street to a small alcove with a Virgin Mary and a lot of needle pins. Legend has it that young girls would go to this chapel and drop a pin in front of the Virgin Mary to pray for marriage.
Universidad de Castilla-La Mancha and Círculo de Arte
The University of Catilla-La Mancha is ironically in an old jail. The windows are barred, the building looks imposing. Is Toledo trying to say something about the similarities between college and jail?
Next to the university is the smallest alleyway in Toledo. Take it to find the convents and quiet areas for prayer.
Next to this alleyway is the Círculo de Arte, which hosts art, theater, movies, and concerts. It’s free to enter during the day for art exhibits, but a charge comes later at night when this art center turns into a disco! The disco is open until 7:00 am. Even more ironically? The Círculo de Arte used to be a church. Is Toledo trying to say something about churches and partying in discos?
Convent of San Agustin
The Convent of San Agustin is a former hotel in Toledo, where the likes of Ernest Hemingway, Albert Einstein, Madame Curie, and other famous intellects stayed when they visited Toledo to learn about the history of the old Spanish capital. Walk in the footsteps of greatness in this convent!
Across the street from the convent is a touristy market where you can eat. It’s a multi-floor gourmet food market with a vertical garden and rooftop terrace. Prices are high, but I guess you’re paying for the experience. I did not stay to eat there.
Ziplining
I am a newer fan to ziplining, and terrified of heights. But…when in Toledo…
Make your way to the Puente San Martin on the western border of Toledo. It’s a beautiful pedestrian-only bridge, and the location of Fly Toledo, where you get harnessed up and fly across the Tagus River. The line is short but thrilling, and you can pose for a picture at the end. Even in the cold, it’s worth it!
Ziplining costs 10€, plus 3€ if you want the photo at the end.
Caves of Hercules (Cuevas de Hecules)
The Caves of Hercules are a subterranean vaulted space in the middle of the historic city that dates back to Roman times. The space was below the Church of San Ginés until 1841. Now, you descend down a circular staircase into the depths to see these ancient caves. It’s free of charge and only takes a few minutes to enjoy.
Other Points of Interest
A few places I didn’t make it to might be of more interest to you. First, in the Jewish quarter are two famous synagogues: Sinagoga de Santa María La Blanca, the oldest synagogue building in Europe still standing and now preserved by the Catholic Church; and Sinagoga del Tránsito, the last synagogue of the 15th century and famous for its rich stucco decoration reminiscent of Sevilla’s Real Alcázar and Granada’s Alhambra.
Also in the Jewish quarter, the El Greco Museum celebrates the Greek painter and sculptor El Greco, who spent much of his life and painted most of his famous works while in Toledo. The building of this museum depicts El Greco’s 16th-century house with a courtyard and garden.
The Museo del Ejercito (Army Museum) is in the bottom level of the Alcázar. Here you can find Spanish civil war toy soldiers, a model of the Alcázar after the siege, military uniforms, and other artifacts from Spanish military history. If you are interested in military history, you could spend hours here.
The Hospital de Tavera was built in the 16th century by Cardinal Tavera. Contrary to its name, it houses artistic collections, the section of nobility of the National Historic Archive, and a church with the crypt of Cardinal Tavera. The palace-museum includes part of the old hospital, and a beautiful courtyard in the center.
The Albergue Castillo San Servando is a medieval monastery and castle across the river from historic Toledo. It was once occupied by the Knights Templar but now serves as a youth hostel.
Across the river and accessible by the City Sightseeing Bus are great photo opportunities of historic Toledo from afar, as well as close-up views of the cigarrales. A cigarral is a summer house or recreational mansion for the Toledan bourgeoisie on the outskirts of Toledo. You can rent rooms in some of these cigarrales for a unique perspective on Toledo. Also near to these cigarrales is the Restaurante Hierbabuena (Peppermint Restaurant), which is known for its organic, fresh, and local foods and exceptional views of historic Toledo.
Where to Eat and Drink
Toledo has so many options to grab a bite or a coffee or a glass of Spanish wine that it might be overwhelming at first. You might find yourself getting off the City Sightseeing Bus in Plaza Zocodover and just stop at the first place you see. Don’t do that! Go out of the tourist area for some of the best Toledo has to offer.
Cervecería El Trébol
If you’re looking for great tapas with great friends, interesting in meeting new friends at the busy bar, or grabbing a solo snack with good people watching, Cervecería El Trébol is the spot. It’s always crowded, so get there early. It’s right off Plaza Zocodover, and well worth a visit any time of day. Try the papas bravas!
Bar-Restaurante Santa Fé
If Cervecería El Trébol is full and you want some authentic Spanish wine and food without the glitz and glam, walk down the street to Bar-Restaurants Santa Fé. It’s not fancy but it’s the perfect place to grab an open table or sit at the bar and get small tapas, perfect for one or two people. The prices are right, the food is delicious, the people are friendly, and the service is spectacular. Try a bocadillo with tomato and jamón serrano – my favorite thing in Spain!
Niño Malo
For a real meal that’s more than tapas, head over to Niño Malo, right off Plaza Zocodover. With inside or outside seating (and heat lamps!), the atmosphere is just right. They have a menu of the day or a full menu for dinner. As much as I love Spanish tapas, sometimes you just need real food. Niño Malo hit the spot. It’s a little pricey being so close to the touristy section of town, so after your meal head over to the convenience store next door and grab a can of cerveza or bottle of wine for cheap! And while at Niño Malo, try the pineapple chicken skewer with honey mustard. Sounds strange, but tastes amazing!
Café y Tapas
I don’t recommend this Spanish chain, but I will add it since I caved and ate here. It’s so tempting to grab a seat and watch all the action in Plaza Zocodover, but the food is overpriced and you will probably leave hungry. I also got approached by a bum asking for money while sitting at the outside tables. The people watching is good, being in the center of the action is nice, but this spot is not worth it.
Mercado San Agustín
Again, another place I recommend skipping over, but I will add it for atmosphere. Whenever I see a food market, I love to try it. It’s a multi-level restaurant with a rooftop terrace and vertical garden. Sounds cool, but I walked into Mercado San Agustín on a Friday around 9:00 pm and it was empty, which is the first bad sign. I checked out the menu and saw all tapas, but the tapas were 17-20 euros (very high for tapas in Spain). Eating by myself, this was out of my price range. And unfortunately, everything looked fried or unhealthy on the menu, so I left. If you’re looking for shareable tapas at the right price, go back to Cervecería El Trébol or La Tabernita.
Bocadillo Takeout Shop
When in doubt or on the run, stop in one of the quick takeout sandwich shops! You can find them on any of the main streets in Toledo. A bocadillo with Spanish ham is 3.50€ or two for 6.50€. Perfect for eating and window shopping, running to your next tour, or just satisfying a Spanish ham craving!
Círculo de Arte
Finally, for drinking, check out the Círculo de Arte building! It’s an arts/music/theater building during the day that turns into a disco at night. I never made it out at night since I was in town by myself, but check out this article on the popular disco (with pictures)!
Where to Stay
Next, on to the neighborhoods of Toledo. This is an easy one. This historic district!
Toledo’s historic district is actually very small and easily walkable. I think I walked across the entire city four to five times a day in about 20 minutes. Plaza Zocodover is pretty central, as is the Primate Cathedral. Both are about an 8 minute walk from each other.
If you’re looking to stay in all the action with people, lights, and touristy things, stay close to Plaza Zocodover (northeast section of the city). It will be a short walk to your hotel or AirBnB (for $30 off your next AirBnB booking, click here) and taxis can drop you off right at the Plaza. You will be in the middle of everything, but you might also hear all the noise beginning earlier in the morning.
If you want to stay in a more residential area but still close to everything, look closer to the Catedral Primada (southern section of the historic city). I stayed in this area and I felt it was perfect. It’s close to sightseeing but still only an 8 minute walk to Zocodover. There are some nice, cozy, intimate restaurants nearby, but remember they are more likely to run on Spanish time (meaning they don’t open for dinner until 9:00 or 10:00 pm).
If you’re interested in the Jewish history of the city, opt for the Jewish quarter (northwest section of the historic city). Calle San Tomé in this section is a popular street with bars, restaurants, souvenir shops, and even a convent that sells candy made by local nuns.
So that sums up my recommendations for Toledo! Have you been to Spain’s old capital city? What did you do while you were there? Tell me your thoughts on Toledo in the comments below!
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