Toledo: Two Days in Spain's Mediaeval Marvel
Two days in Toledo, Spain. How hard could it be?
Well, when I arrived in mid-August of 2026, the temperature was a balmy 40°C (104°F) at 7 p.m. As I posted that evening, this was not weather. It was an oven. No, not even an oven… perhaps a furnace? Nope… Let’s go with the fiery pits of Hell with gorgeous architectural landmarks.
And that pretty much set the tone for my two days of adventuring in Toledo.
I had visited this magnificent mediaeval city 13 years earlier with my mother, so I was curious to see what it would feel like to return to a city that I simply recalled as being “gorgeous”. Over the next two days, I wandered through 1500 years of history, admired masterpieces by El Greco, sampled some very fine Manchego cheese, stumbled upon unexpected treasures (above ground and under it), chased down pastries hidden behind ominous doors, got caught in the rain during the worst possible time, and developed a rather extensive system of ratings for the places I visited and food stops I dined at.
Some experiences were spectacular. Some were decidedly “meh.” And at least one made me suspicious of my mother’s desire for unique handmade souvenirs.
So, if you’re wondering how to spend two full days in Toledo, come along for the adventure. Just remember to bring comfortable shoes, an appetite, a sense of humor, and the willingness to invest €5 in an “abanico”, (aka a folding fan), and develop the necessary skillset to unfurl it at lightning speed like a true Spaniard.
Toledo: A Quick Guide
- To reach the city, simply take a 30 minute train from Atocha Station in Madrid.
- Best for: history lovers, photographers (be sure to explore after sunset because the night photography is pretty magical!), and foodies
- Walking difficulty: high (lots of hills, not easy for those with mobility challenges!)
- Don’t miss: El Greco’s Burial of the Count of Orgaz and El Trébol for some of the best food in Spain (no joke!)
- Best surprise: hidden churches and unexpected discoveries, like the Church of San Román
- Allow time to wander around because you never know what you may stumble upon
- Biggest challenge: summer heat, seriously it could feel like a hair dryer is blowing on every inch of your skin if the wind picks up
- One or two days? Definitely dedicate two full days to this fabulous city! But, if you are tight on time and the alternative is simply not to go at all, then, yes, the highlights can be visited during one incredibly long and exhausting day trip from Madrid.
Toledo Itinerary: A Personal Travel Diary with Brutally Honest Reviews
Toledo: Day 1
Well, today was fun! 😄
I had a nice little breakfast at my charming temporary residence, Hotel Boutique Adolfo, before setting out into the already 35° Celsius heat for the cathedral.
La Catedral Primada de Toledo is hitting a major mile marker this year, it’s 800th anniversary. So how extraordinary it is to be able to visit it during such a key moment in its history!
I had visited the cathedral 13 years ago, but this time it was a little underwhelming. But, perhaps surprisingly, I’m quite grateful for that. Much of the interior of the cathedral was being refurbished and was, subsequently, blocked off from viewing. Furthermore, the construction work was quite loud. Oh well, I still enjoyed myself because there were separate rooms containing some beautiful artwork, including a very striking painting by Caravaggio.
Overall rating for La Catedral Primada de Toledo, 7/10 because the artwork was nice (but lacked information beyond the artists’ name and year of production), but it would have been nice if the loudest of the construction noises could have been conducted before the cathedral was open.
I then proceeded to the Museum of Manchego Cheese right down the road from the cathedral. It was a small museum, but it adequately covered the history of the famous cheese that has been produced in Toledo for centuries. I then enjoyed a pleasant tasting of three different aged Manchego’s with some black garlic pimento marmalade and a Tinto de Verano. It was a very scrumptious cheesy experience. 😋 Before departing, I purchased a vacuum-packed semi-aged Manchego and a couple of marmalades to bring back to LA.
Overall rating of the Museum of Manchego Cheese, 8/10 because there was interesting information in English, I never felt rushed, and I was grateful to have the opportunity to purchase some cheese and marmalade to bring home. The lady explaining my tasting plate wasn’t able to do so in English (or maybe she just didn’t feel comfortable trying), which would not be very helpful to tourists who don’t understand any Spanish at all. My Spanish language skills are adequate at best, so it wasn’t too big of an issue for me personally.
I followed this with a visit to the Synagogue of Santa María la Blanca. It was constructed by Jews in Moorish style under the rule of the Christian Kingdom of Castile. From a photographers perspective, it was absolutely stunning! Small, but elegant and a sheer pleasure to photograph from multiple angles.
Overall rating of the Synagogue of Santa María la Blanca, 9/10. I can’t give it a perfect score because it was so bloody hot inside. At least putting some portable fans inside to circulate the air would have been appreciated.
On my way back to my hotel, I stumbled upon a building that said something about Visigoths. 
Intrigued, I entered through the open door and WOW! Inside was a gorgeous Mudéjar church filled with Visigothic artifacts and 13th century Romanesque frescos. 
Just another reminder that when you’re traveling in Europe and you spot an ajar church door, walk in. You never know what you may find!
Overall rating of the Church of San Román, 8/10 because it’s unique and really, really cool, even if you aren’t normally interested in history. I would have liked to have seen information in English.
After a midday siesta, I returned to our favorite restaurant from 13 years earlier. Cervecería El Trébol was still just the same. Filled with young people and fabulous food for a great price. And my sweet waitress brought me a free delicious tapa to go with my sangria. 
Overall rating of Cervecería El Trébol, 10/10 because it is quite honestly some of the best food I have ever had in Spain, and I lived here for three years and in three different cities and provinces. Cervecería El Trébol stands out from almost any of them!
Content that my day would finish early, I returned to my hotel. But the excitement was not finished!
Sometime around 8:45 in the evening, I began to hear a commotion from my room. Drums in the distance. 😳 I rushed to my little balcony, and sure enough people were lining up. A parade was coming! 😯
This wasn’t the first time I had a parade walk by under my window in Spain, but this parade was something else altogether. Fun, intense, loud, and joyful. It was called the Desfile de Gigantes y Cabezudos or the Parade of Giants and Bigheads. 😂 Well, at least the name was suitable since there were giants and characters with big heads.
Toledo: Day 2
I was a very, very busy little bee today. 🐝
Breakfast at my hotel was even better today than yesterday. Jamón Ibérico, Manchego, tomato toast with extra virgin olive oil and salt, pistachios, yogurt, a warm chocolate croissant, an assortment of fruit, and freshly squeezed orange juice. 😯
Thankfully, the weather was cooler. I started off with a visit to the Iglesia de Los Jesuitas where I was able to climb its tower for a decent view over the city, but I was difficult to take photos through the steal mesh. Overall rating of Iglesia de Los Jesuitas, 4/10 because it was kind of “meh” and the tower wasn’t like a classic church tower that is fun to climb. At least the view was OK.
I followed this with a pleasant meander through the narrow streets in search of the masterpiece of Toledo’s most celebrated artist, El Greco. Boy did it not disappoint! It’s called El Entierro del Conde de Orgaz or the Burial of the Count of Orgaz (1586-1588). The colors seemed so carefully selected; the mournful expressions on people’s faces were quietly moving, except for one boy who is staring at the viewer intently as if challenging you to look away from such a solemn scene. It is simply a powerful painting.
Overall rating of El Entierro del Conde de Orgaz, easily 10/10 and should not be missed.
I continued on my journey with El Greco at his museum right down the road. Numerous of his paintings were on display in his old home. The 12 disciples all depicted in their own paintings were beautifully unique. I particularly liked St. John the Evangelist presented with a golden goblet with a little dragon-looking thing inside it.
The El Greco Museum also has some lovely gardens, and I was even able to spend time with two of the garden cats. 🥰
Overall rating of El Greco Museum, 9/10 because it had a nice flow about it, meaning that it didn’t seem jumbled up, and it contained some of his best artwork. I would have liked to have been able to watch a short video about El Greco that could have at least had English subtitles. The gardens were simple but nice and had a few benches to relax on.
After dedicating ample time to El Greco, I stumbled upon another church that caught my eye. A sign in front of it mentioned that the church stands where a 9th century mosque was originally located. But below the foundations of the church are Late Roman and Visigothic archaeological remains. So, of course, I had to go explore. Most people wouldn’t find such remains interesting, but I did and particularly liked seeing the different layers and materials used in the Roman age walls.
Overall rating of this church called Iglesia de Salvador, 3/10 because it was very simple and not ornate enough to impress me. Really, the only cool thing about the church was what was underneath it.
Feeling the need to dine at a popular local spot, I went to Bar Skala. It was hot, busy, and simple inside. But this place was rated very highly on TripAdvisor. I tried to order two small dishes, but the waitress just shook her head and told me I was ordering too much for one person. 
Like, girl, I’m just trying to order what everyone else is ordering. But she was adamant. So, I got whatever it was she recommended. It was some sort of cheap meat with peas guisado/stew. It wasn’t bad, but not that great either. Oh well, I tried.
Overall rating of Bar Skala, 5/10 because the food was decent, but they were out of one dish that I really wanted to try, the waitress would not let me order an alternative because she thought it was too much food (guess what, it wasn’t), and it was hotter than the bowels of Hell inside. The music playing in the background was authentic and fun though.
I then spent way too much time trying to find the entrance to the Alcázar before it closed. The entrance ended up having a completely different name for the museum.
I was hoping the Alcázar was going to have a nice view over the city, but no, it barely skimmed the tops of the roofs. The rest of the museum was dedicated to Spanish military history, an area of academia I have little interest in. So, it was a waste of €5. Overall rating of the Alcázar, 3/10 because I found it incredibly dull and boring. A short optional film about the most significant exhibits on display or key points of Spanish military history would not have been out of place for visual learners like myself. (If you want to see a truly stunning Alcázar, then visit the one in Sevilla.)
Following this, upon a request from my Mom, I was sent on a wild goose chase to find a hidden door to a hidden convent where the nuns sell homemade pastries. If only I could make up such things!
The “hidden door” was not located where it was supposed to be, however there was a sign conveying that it existed and that I would have to go down a narrow, creepy alley. 
The things I do for my mother… I made my way down the narrow, creepy alley until a sign said I had arrived. I rang the bell and waited and waited. Nothing. 
So, I inspected the door a little more closely and found another sign at the very top that mentioned that the pastries could be found at another address. 
So on to the other address I went. I walked down another alley that led to a dead end with an old wooden door, once again with a sign saying that I had arrived. 
I rang the bell and waited for probably 20 very uncomfortable seconds. A woman’s voice popped into the intercom. I hurriedly told her my intentions, and the old wooden door magically opened to a long, mostly bare hallway, with nobody in it.
Behold, the moment where every horror fan screams at the protagonist to not go down the ominous hallway in a hidden convent, especially alone. But, hey, I guess I’m just dumb, or perhaps I haven’t yet seen a scary movie where the protagonist gets axed by a pastry chef/nun. Once again, the things I do for my mother. So, I stepped over the threshold and cautiously made my way down the hallway.
At the end of the long hallway and around the corner, a nun was waiting for me. I greeted her nervously and she pointed me to a small glass case with little pastries held within. I requested the only batch of pastries that had the sticker for the convent on it, hoping that it would satisfy my Mom. It cost just €7.
I thanked the nun and she responded with a terse demand to make sure I closed the door on my way out. Sí, Sister! 
So, that was an interesting adventure. 
Overall rating, 7/10 simply because the experience was unique and I survived to tell the tale.
I then proceeded to take a little motorized train that I had ridden 13 years ago. It takes you up to a vista overlooking the city and gives you information about all the landmarks we pass. Unfortunately, I sat on the left side of the train where I could essentially see nothing. 
And by the time we reached the vista for a short photo stop, it had started to rain, considerably. Typical. I grabbed some photos anyway.
Overall rating for Toledo Train Vision, 6/10 because the information was interesting and offered in multiple languages, but they really need to do something to enable people on both sides of the train to see the scenery and take photos, even if it’s on the way back into town. (Just for fun, below I included two photos of me with the train from 2013 and 2026.)
Knowing that I had yet to purchase some marzipan for my Mother, as purchasing sweets from Nuns was not enough for her, I researched where to find the best marzipan in the city.
And on I went, racing to the number one rated marzipan bakery in the Jewish Quarter, in the rain, weaving in between people, before it closed.
The purchase was successful and I was sent on my way with a free sample of marzipan which was very almondy and yummy.
Overall rating of Mazapán Santo Tomé, 10/10 because they had lots of options to select from, it was really pretty inside, I got a free sample, and, after I told them it was a gift for my mother, they wrapped up her box of marzipan in beautiful wrapping paper without me asking.
I was exhausted by that point, but I still had two more objectives to accomplish: video chat with a friend so she could see the city and return to El Trébol for a late dinner.
I showed my friend around, impressed that I was miraculously able to navigate through the maze of winding streets without my maps.
Then I returned to El Trébol once more. As I entered and went to grab a seat, one of the waitresses looked at me with crazy eyes like I was some disgusting cockroach. She yelled at me that I had to wait. Like wtf for? 
Nobody was ahead of me waiting for a table, and the place was happily buzzing. I hurried downstairs instead and grabbed a free table. A nicer waitress greeted me, but even she had to get “Crazy Eyes” involved who yelled at me again demanding to know if I was there to eat dinner. 
Like, no, I’m there just to piss you off lady. It was so stupid and unbelievably rude.
Anyway, I ordered a drink, some more patatas bravas, and a truly mind-blowing venison stew. I was feeling adventurous and thought it might shut up “Crazy Eyes” because what kind of female tourist asks to eat Bambi? 
The food was still a 10/10, but “Crazy Eyes”, she gets a big fat 0.
I got back into my room at precisely midnight, but Toledo was still humming with activity.
After two very full days in Toledo, I can safely say that I walked 12 miles, ate my weight in patatas bravas, got rained on (during a heatwave), got lost (and found), stumbled upon things I wasn’t looking for, and somehow managed to survive a solo expedition into a creepy hidden convent in pursuit of €7 worth of pastries for my mother who may have questionable intentions.
So, all in all, I’d call this excursion a success.
Toledo isn’t the kind of place where you need to follow a perfectly organized itinerary from one major attraction to the next. Some of my favorite moments came from simply wandering through its winding streets and following my curiosity when something caught my eye. A random open church door led to Visigothic artefacts and mediaeval frescoes. A sign about archaeological remains led me underground. And a mysterious door in a creepy alley led, eventually, to a very serious nun and a box of pastries.
Of course, not everything earned a 10/10. Some attractions were underwhelming, some meals were merely okay, and apparently even returning to one of my favorite restaurants from 13 years ago comes with the risk of being yelled at by a crazy-eyed lady. But that’s traveling for you. The memorable trips aren’t necessarily the ones where everything goes perfectly; they’re the ones where you come home with slightly awkward stories, pleasantly dramatic photos and videos, and a tummy full of Bambi.
Would I return? Well, funny enough, I’m heading back to Spain in a couple of months, this time with my Mom in tow. And, of course, she insists on returning to Toledo. I have little doubt there are still more churches to wander into, more secrets to uncover, more tapas to try at El Trébol, and, apparently, more pastries for my mother to track down.
At least next time, I’ll know my way around.
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