a guide to toledo, spain
published in passerby

Only a half-hour train ride from Madrid, Toledo is a quiet Spanish haven and historical hub with something for everyone.

Renowned for the preservation of its Old Town and its compelling Christian, Muslim, and Jewish heritage, spending any amount of time in Toledo is set to delight history buffs and architecture enthusiasts, but it’s equally bound to nurture anyone wanting to get lost in the cobblestone and take it slow. A visit in February – March or October – November is ideal to avoid tourist floods and curve unfavorable weather; you can find warmth even beyond summertime, as the Toledo sun shines with force whenever it’s out.

what to see

You won’t need a guided tour to grasp the cultural depth that defines the city. That being said, it’s well worth your time to make visits to some core sites for religious architecture. My favorites include the Synagogue of El Tránsito in the Jewish quarter (which offers free admission on weekends), the Convent of Santo Domingo El Antiguo featuring work by El Greco, and the Cristo de la Luz Mosque dating back to 999. Of course there's Toledo’s notorious Cathedral as well, but I believe in giving other spaces some love, too.

I always gravitate towards contemporary art over all else, so the Roberto Polo Collection brings me joy when Toledo’s aesthetic deviance from contemporaneity starts to feel heavy. Offering free access, the gallery is set up like a maze with a defined pathway to encourage a mindless flow through the works. And, they have a sweet curation of chairs on display (including this one by Eileen Gray, which I was so thrilled to see).

I gave the Torture Museum a shot, too, even though I normally avoid spots that feel like tourist traps. I found it to be a really fascinating way to learn more about the Spanish Inquisition, as the history and timeline are presented through the lens of how each contraption functions. It’s unsettling and bizarre, but I’d definitely recommend.

I think any local would suggest visiting la Biblioteca de Castilla-la Mancha, the regional library here, as it’s located in the heart of the city and central plaza, and it’s renowned for having the best view of Old Toledo. I’d concur, and would add that their cafe –– which sits on the sky-high top floor –– is a quality spot for a 1€ beer and a satisfactory tortilla española. 

what to do

I’m embarrassed to admit how many times I've ended up at Medina Mudéjar, but no frequency could ever overdo it. You can find Arabic baths all over Spain, and they’re just so inexpressibly dreamy — truly fit for romance, friendship, or solitude. Whatever you need. You’ll encounter small pools of different temperatures (spanning hot to warm to cold), a steam room to bask in between each, plus complimentary cookies and tea set out for you. A visit here is also in order for anyone looking to learn more about Mudéjar architecture.

I’m not sure if anyone relates, but I love trying haircuts in new cities, and I’m so glad I did in Toledo. A haircut at Frann is like a work of performance art conducted by a true artist whose process is laced with such drama, sharp movements, and twirling that it’s hard to put into words. On top of that, I was completely pleased with the final product: an amazing micro-bang, curly chop, and full-on show for 30€ and in only 30 minutes.

Perfume shopping is another favorite way to feel out a fresh environment, and I often like to purchase a fragrance during my travels as a sort of aromatic document of the trip. Whether you’re in the market for a high-end perfume or a more affordable one, Toledo accommodates. Visit Florence-born Aqua Flor in the Jewish quarter for the former, which offers a strong selection of florals and is so pleasant to spend time in, if nothing else. For the latter, I’d recommend Fragancias, which offers 6€, natural dupes to just about every designer fragrance. They have an extensive catalog to guide your hunt, and you can upgrade your purchase with adorable little floral-printed bottles for an additional few euros.

Toledo is incredibly sparse when it comes to shopping for clothing, so I never found anything truly up to standard for my vintage and antique cravings (a helpful reality for limiting spending, I suppose). There are still a few spots for antiquing that I’d recommend, though. You can find a wonderfully overwhelming maze of ceramics at Cerámica J Serrano and miscellaneous tchotchkes, from charms to jewelry to vases to tins to religious artifacts, at Brocante Toledo. I also adore the jewelry at C. Trinidad, 6; the owner Beatriz is so lovely and has a great eye.

must-try food

Spain is so bread-intensive that it’s impossible to spotlight only one bakery. My top picks for quick stops are Benipan for spanakopitas and Leche y Pan for napolitanas. If you’re looking to sit down, Teteria Dar Al Chai has a cozy interior and the best savory crepes, while Masa Madre makes a great carrot cake that you can enjoy in a quaint courtyard with colorful seating. And artisan Abigail Cohen is a must for picking up Sephardic-Jewish pastries.

A go-to brunch spot, I’ve been served the best orange juice of my life at Cafetería la Pepa. It’s a true gem for can’t-go-wrong basics if you’re struggling with heavier Spanish food. The yogurt is unreasonably good also.

In addition to its mesmerizing multiple floors, warm ambiance, and comfortable booths, I’ve frequented the treasure that is Restaurante Marrakech for the 5€ shawarma, the charming owners, and the versatility –– it’s a reliable choice for a solo lunch or a night with friends (with shisha).

La malquerida is easily my favorite going-out destination in Old Toledo. They defy siesta culture and are not only open all day and into the night, but they’re completely alive at all hours. As another pull, you can find fresh vegetables and salads here, which was strangely hard to come by elsewhere (ha).

La ermitaña is a nicer option with a gorgeous view of Old Toledo. You can’t quite walk to it from the main plaza (without conquering a mini-hike), but it’s worth it for high-quality seafood, perfect vegetables, and a classier mood. Definitely fit for a special occasion.

drinks, from coffee to cocktails

I sincerely believe that the best coffee in Toledo awaits you at Il cappuccino. On top of a quality product, though, the barista is really knowledgeable and passionate, which makes for a nice moment of conversation and coffee-education. The café con leche was my go-to.

If you know Spanish, I highly recommend the tasting room at Museo del Queso Manchego for anyone curious about cheese and wine from the region. You can even drop in for a glass and a small plate at the price of only 5€, featuring a little crash course on what’s in front of you from the owner (who’s really delightful).

Like shopping, Toledo’s nightlife is sparse. I’d recommend planting at a restaurant (like La malquerida) for a fun night over scoping out the bar scene, but your best bet for a more standard bar is O’Brien’s. It’s really just your average Irish pub, but it’s incredibly central to the main plaza and guarantees a good time with good music.

If you’re eager to dance, Círculo de Arte is a church reimagined as a club, which makes for a funny spirit and feels on-brand for Toledo. I’d say it’s also the least grimy and least university-dominated club in the city.

final thoughts

My months spent living in Toledo disturbed my United States upbringing in all the right ways, mostly in the sense that I learned how to move slowly for the first time. I gradually departed from my to-do list fixation, my self-inflicted pressure to be punctual without fail, and my unnecessary aversion to sleeping in (for the sake of granting myself a productive morning).

But this slowness was forced upon me, which is the coolest part. Toledo is small, and it’s incredibly Spanish in its complete devotion to the 2:00-5:00 siesta, to the extent that it feels virtually impossible to access anything other than the town’s only Starbucks in that timespan. I was pushed to make my way home and just rest each day (unless I elected to lay in a park instead). Peace is completely wired into Toledo, and time spent on its premises makes that hard to ignore and hard to refuse.

With slowness also came space to prioritize meaningful connection with and consciousness towards all of what surrounded me. I felt incredibly clear and mentally available to enjoy the coffee I sipped and the many heartwarming storeowners I crossed paths with. Forever holding onto my soaks in the Arabic baths and my daily bread fix.

So while other corners of Spain like Barcelona and Madrid are set to provide a high-energy experience with lots to stimulate, I encourage a visit to sweet Toledo, too. You likely won’t fall into a wild night out or pick up much style inspiration, but you’ll surely recharge and cherish the breath of fresh air, which completely transformed me for the better.

Images by Eva Berezovsky