To get to Toledo, my fiancé Tony met up with me in Madrid around 3PM and we headed to the Atocha train station to hop on our 3:50 train. 35 minutes later I said, “Holy crap I can't believe we're already here” to which Tony responded, “Holy Toledo!” And thus began our adventure in this beautiful little town on the hill. Even the train station is ornate - the exterior has incredible detail and the main internal wall is covered in stained glass and mosaic tiles. I knew if this was any indication of what the city might look like, I was about to be seriously impressed. From the train station Tony and I opted to do the 20-minute walk up the hill into the old city and even with our backpacks, it was well worth it. On the walk there we were exposed to fantastic views of the main entry into the city and the Alcázar located at the highest point.
Once at our hotel, we dropped our bags and headed deeper into the city to explore. There are very few “main” streets in this city which made for a fun walk as we twisted and turned our way around. We headed to the main gothic Cathedral (Catedral Primada Santa María de Toledo). It's pretty ridiculous. We didn't, but if you want to go inside, you can also see a number of works by El Greco who lived in Toledo for more than half of his life in the late 1500s.
From here we wandered over to the Mercado de San Agustin where I had heard there was a cool rooftop bar. It was nice, but I definitely think there might be a better place to hang out at dusk (keep reading!). From here we went to our dinner reservation which I was VERY excited about. We had made a 9PM dinner reservation at Restaurante Tobiko. We arrived at 9:15 and were the first people there. Oh, Spain and your refusal to eat dinner before my bed time. We enjoyed the Menú del día which included fresh bread, an appetizer, entree, dessert, bottled water and a shared bottle of wine. This meal was €20 each, massive, and delicious. I had the croquettes (best I've had in Spain), steak, and raspberry-cream-cheese dessert. This restaurant is not in the old city, so it's about a 30 minute walk or €10 cab ride (we did one of each), but it was well worth it.
In the morning we skipped a run since our feet were pretty tired from close to 10 miles of walking the day before, but once we got out for our morning, we were bummed we did. There's this awesome trail called the Camino Natural del Tajo that runs all the way around the city and while we enjoyed some of the views that trail has, we can only imagine what some areas might have looked like. In the morning we walked out of the old city back so that we could reenter it on the Puente de Alcantara (the running trail goes right under this bridge). From the bridge, you climb a bunch of stairs and are able to see and explore the top of the city wall all while keeping the Alcázar in sight. At the top of the stairs there's a restaurant called Terraza del Miradero. We stopped for a coffee, but this would have been a great place to stop before a dinner reservation :).
For lunch we made our way back to the Mercado de San Agustin which, along with the rooftop bar, also has 12 small cafes. We stuck to the bottom floor, and were pleasantly surprised that any of the places will let you bring food/drink in from a different cafe. We had a lunch of champions - pizza (sub-par) and chocolate cake (best we've found in Spain... not kidding). From here we did more wandering through the city towards the Victorio Macho Museum which we were going to go to for the views before discovering that the views are free just outside the museum (win!).
There are tons of shops around Toledo selling swords and painted tiles and ceramics. Most looked pretty mass-produced, but we were impressed by Pincel y Barro and learned a tough siesta lesson when we tried to stop in to buy a few items before leaving town (siesta is real, people!). Bummer.
Around 4:30 we started heading back to the train station to catch our 5:25 back to Madrid. From there we would take the subway to the other Madrid train station and grab our train to Segovia.
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Guide includes including walking maps, running/hiking routes, and restaurant and tour information for Madrid, Toledo, and Segovia.