Until you’ve seen Toledo, you have not seen Spain {a famous Spanish saying}. Ah, Toledo – I only got to enjoy walking around your beautiful cobblestone streets for one night and one morning but one thing is for sure – you certainly know how to leave a great first impression.

The reason I happened to be in this UNESCO heritage site in Spain only 30 minutes from Madrid was due to it being the perfect stop during our #winteroadtrip from France to Lisbon, Portugal. Like any good American, I love road trips and this one was as pretty as any I have ever been on. For those who doubt me, the drive from Ax-les-Thermes to Toledo looked a little like this.

Crazy, right? I had no idea that Spain is Europe’s most mountainous country after Switzerland. During the drive I snapped my photos with a resounding wow | ouah | stupenda in a variety of different languages as we made our way down highways A-2 and E-90. Driving down this stretch of the highway was one of the prettiest road trips I have ever been on, lush landscapes, mountains and tons of toro (bull) signs at every angle.

After a very pleasant 8 hour drive, no sarcasm on this one – we finally arrived at our destination for the night, the city of Toledo in the Iberian peninsula. Emperor Carlos V once said in 1556 that Toledo is a place where the sun never sets and he might just be onto something. The architecture of this walled town is very unique in Spain and likely due to being slated as the “City of the Three Cultures”, having been influenced by a historical co-existence of Christians, Muslims and Jews before 1085.

Because we were driving what can only be described as an airplane (no joke the front windshield was reminiscent of a Boeing 747), parking was a bit of a challenge in this town of steep, windy and tiny streets. Luckily after a few fumbles, we managed to park temporarily and find our hotel before moving the car to a recommended public parking lot for the night.

Apparently during our 8 hour drive, www.booking.com failed to tell us that our hotel’s reservation had changed and that instead of staying at the rustic place we planned to in the center, we were moved to another hotel as soon as we got there. The owner of hotel #1 assured us that the other hotel was ‘much much better’ (not sure how great his self-marketing is) so we sighed and headed on over. I was a tad annoyed and a bit sketched out until we finally saw our room (which was pretty basic) and more importantly our amazing view!

Alright, no complaints to be had. Since Nico was nice enough to take on the trauma of parking the car, I decided to get us a bottle of wine to properly celebrate our first night in this gorgeous town. This vacation can officially begin!

We spent the rest of the evening before dinner strolling down the beautiful cobblestone streets among all of the swords and bracelets for sale in every window. Toledo was famous for the craftsmanship and quality of their swords to the point where even Hannibal had to have them.

On a girly note, I especially liked the black and gold bracelets and I do regret not buying one to this day, I am still thinking about how pretty they were. However, this does mean I have to come back. Of course we ran upon a Spanish ‘churruria’ – a fast food stand for everyone’s favorite churros. The man serving this crispy, sweet treat looked rather enthusiastic as he served up these tasty delights. 😉

Of course no European adventure would be complete without running into some sort of random musical concert. This is what I live for, and naturally we caught the magic.

[youtube=http://www.youtube.com/watch?v=VDPqTn0iSWc&w=560&h=315]

Cava and Tapas – a foodie dream 

Obviously this girl is all about food, I am pretty sure my family back home is convinced that I don’t actually have a job and all I do is go to restaurants all day long {um yes please, I wish!}. While I do plan on being the next wo(man) vs. food, I do have other hobbies, like drinking. Of course the Spanish love to chow down as much as anyone and I scoured the streets for typical foods from the region.

Meat and game play a big protagonist due to nearby game reserves and though I didn’t try it, quail is recommended dish. We ended up going to a lively restaurant in plaza san nicolas and started with a gin & tonic {super trendy cocktail in Spain}. Dinner was in the cellar and we indulged in some cava {spanish prosecco} and a variety of tapas-like dishes. My standout favorites was the baked eggplant topped with a beautiful goat cheese and honey, sprinkled with pistachios. We also got a dulche-de-leche type cheesecake that was perfection. It was by far the best meal we had in Spain besides Bilbao.

La Abadia Plaza San Nicolas, 3, 45001 Toledo, Spain Prices around 20-25 euros/person with cava, shared tapas & dessert. Plus 5 euros for a fabulous gin & tonic ;-).

The next morning we got up bright and early in order to check out the town before setting off to Lisbon. The sun was out, the air was crisp and cool and I was beyond ready to sneak down every tiny alleyway, this city is really so beautiful. Mesmerized, we put the map away and just walked, cause sometimes that’s the right thing to do.

This is Toledo

 Needless to say this city is UNESCO recognized for a reason. I am super thrilled that we decided to stop here along our road trip instead of busy Milan. It allowed us to relax and unwind after a long drive and discover a new city that I can talk too much about {hence the long post}. I plan on coming back, and I plan on buying that beautiful black & gold bracelet…

Must-sees in Toledo

• The Cathedral of Toledo: A beautiful example of Gothic architecture in Spain, this stunning church makes a great point of reference in this small town. Plaza del Ayuntamiento. Open Monday to Saturday 10h – 18h30 / Public Holidays and Sundays 14h – 18h30, €7 entry, tel.: (+34) 925 222 241, www.catedralprimada.es

• The Alcazar Fortress: High up on a hill, a great place to stop for panoramic views of the city and to browse their large municiple library {and military museum}. Calle Unión, €5 entry / FREE Sunday, tel. (+34) 925 238 800, www.museo.ejercito.es

• Plaza Zocodóver: one of the main squares in town, this is where we caught the impromptu musical concert above and is named after a market housed here during Moorish times. Vibrant and yes, a bit touristy – I loved the vibe in this piazza.

• Mirador del Valle: Carretera Circunvalacion, 45004 Toledo, Sp. The best vantage point for getting the best photo of the city.

• Iglesia de San Ildefonso (Jesuitas): Plaza Padre Juan de Mariana, 45002 Toledo, Spain. This is the cathedral where I took my panoramic photos of the city (from the towers above). While not heavily advertised, we stumbled upon this while walking around and were super happy we did. Plus only 2.50 to get in!

Obviously not being a local expert in this city, take a look at this great guide from Conde Nast Traveller. And I want to hear from you! Have you been to this city? What would you recommend as a must-see?