1. Eat and buy tons of manchego
  2. Try some marzapan
  3. Have drinks or tapas at the Parador terrace

Toledo holds a very special place in my heart – it was the very first place that I visited outside of Madrid during my first trip to Spain (and I made the trip alone no less). It’s fairly accessible from Madrid and will satisfy your craving to experience a charming, quintessential Spanish pueblo. With its teeny tiny alleys that wind like a labyrinth, you will find yourself loving getting lost.

A brief history
Toledo, originally discovered by the Romanians in 192 BC, used to be the capital of Spain and therefore at one point was at the center of commerce and movement throughout Iberia. You wouldn’t really know it these days – it’s hard to imagine its narrow little streets packed like Manhattan. Because it is at the center of the country it has been a melting pot for cultures – Christian, Hebrew and Islamic. Once ruled by the Moors, Toledo was then conquered by the Christians in 1085, and then remained the capital until it was moved to Madrid (largely for lack of space) in 1565.

What to do
When you first arrive to Toledo’s Plaza Mayor you will want to pick up a map, although admittedly, it may end up being useless. The city is so confusing, and yet so small, that by the time you figure out where you are and where you need to go on the map, you will have probably ended up somewhere that you want to be. That said, it’s probably good to have one handy just in case. The tourist office is to your left if you are just entering the main plaza.

The spots you won’t want to miss in Toledo are the cathedral, the Alcazar (or the fortress – although note, it hasn’t been open to the public in the three years I’ve been here, due to construction), and just getting lost in the city.

Other hidden spots you might want to check out include two great vista points. One is behind the Alcazar, if you are facing the Alcazar from the main plaza. Head down the right side of the Alcazar to the very back where you will see a gate with stairs that appear to head down the side of the hill. From there you will find many hidden lookout points where you can view the river wrapped city.

Also a fantastic place to grab tapas and sit back and enjoy the view is the Parador of Toledo. It is across the valley and has an expansive view of the city, which you can enjoy from their terrace. I’ve only gone there by car, but surely if you inquire in the tourist office, they can tell you how to get there by shuttle. It’s only about five minutes away.

What to eat
Well, since Toledo is located in Castilla La Mancha, this means it is home to same marvelous manchego cheese. Do yourself a favor and eat a lot of it. You will also notice that many of the pastry shops have marzapan (or mazapan), a specialty of Toledo.

Other cities to visit in or near Castilla La Mancha
Cuenca (Castilla La Mancha)

Experiences from my blog