“If you visit only a few Spanish cities in your lifetime, make beautiful romantic Toledo one of them”.  -Frommer’s Spain Guide 2004

These were the words that prompted us on a whim to take an afternoon day trip to neighboring Toledo.  Only an hour or so outside of Madrid lies the charming Medieval town of Toledo.

Toledo remains of special importance in the Spanish heart with its Arab, Jewish, Christian and Roman influences. The town borders the Tagus River on three sides and affords a spectacular view of the plains of New Castile. Surprisingly it has remained relatively unchanged or untouched over the years yet we did find annoying invaders of modern times creeping in by the tacky souvenir shops and overpriced tourist restaurants. We were all surprised to see all the new and rising generic subdivisions being build on the outskirts of Madrid and en route to Toledo.

We had a map yet found it extremely difficult to navigate the serpentine streets of medieval Toledo. This was going to be a common trend throughout our trip in Spain. Many streets are simply left off the map and we spent a lot of time simply being lost.  Many times that is the best part of a trip.  Getting lost and exploring.  Yet for some reason, we found it annoying this time as we were constantly being stuck behind massive blocks of tour groups. After hours of walking it was time for lunch. We were both famished and had to settle for the closest option, a touristy restaurant nearby the cathedral with overpriced, terrible food.

Lesson learned:  Sometimes the best most highly-rated must-see sites end up being the most disappointing for just that fact.  They are overrun by everyone else who is trying to see them too.

Getting off the beaten path is getting harder…..

Stay tuned….yes I am really lacking photos on this trip but I’ve already committed to writing this series so onward I go!  It may be short but sweet.  All an experiment I guess.


  1. I lived in Toledo for a year from 1999-2000 during an exchange program when I was in university. It brings back so many wonderful memories. The plazas, the school, the couple I lived with at the time. What a special city!

    • I bet that was wonderful! I think going to places like this are best off season too. For some reason when we went it was very touristy. I spent a year in France during my studies. Like you, it was one of the top highlights of my life. Just wonderful! It would have been cool to live in a smaller city like Toledo. I was in Paris and Marseille and then did a summer as a nanny in the countryside.

      • Toledo is incredibly touristy – the father in the family I lived with worked as a security guard at the Alcazar – the fortress on the hill, but it also was a home and a great jumping off point for other travel in Spain. Living abroad is such fun!

  2. So did the city seem as romantic to you as the Lonely Planet claimed? Or was it too crowded?

    I think there is a definite correlation between winding, unmarked streets and romance… if you are in the city in love and without a particular schedule or plan, it’s wonderful to just stroll around and get lost. Otherwise you’ll probably be a stressed out mess!

    • I think I was overall a little disappointed as honestly most all the cities on our Spain trip were so incredibly touristy that it lost a lot of its charm. I had told my husband how wonderful Spain was and was so excited for the trip yet it was really overwhelmed by busloads of tourists. Not sure if it was the timing. We went in May. This was also 8 years ago too so who knows, maybe it was a hot spot at the time. I did find Toledo beautiful though. Just wished it didn’t have so many souvenir and touristy trinket shops. It was also a hard trip because I was 13 weeks pregnant. I was a little too irritable and had to constantly use the bathroom which is not easy to find in Europe….the public loo! Oh well. My favorite place was Granada. I would go back there in a heartbeat!

    • Thanks Angeline! I feel like it is lacking a bit but oh well. I am having fun playing around the the photos! I’ve had to scan the ones I have and then have applied vintage looks to them for an older feel. I have some beautiful ones from Granada and Ronda which will be fun to share. Thanks for the encouragement! 🙂

  3. The notion of not being able to find your way around medieval Toledo streets even with a map is, in and of itself, romantic. What a fascinating place.

  4. I went to Toledo in the summer of 2009 and I had the same observations. It felt so much like an open-air museum and although it wasn’t too crowded everything – even the sights themselves – were completely overpriced. I prefer Segovia, especially late in the afternoon and in the evening after the day-trippers return to Madrid. Did you manage to make it to Salamanca?

    PS forgive me if I’m wrong, but I think picture you have of the cathedral is actually the one in Seville. 🙂

    • Hi James! I loved Segovia as well and didn’t make it to Salamanca but heard it is wonderful. As for the cathedral, I don’t know for sure. I have it in my photo album next to the picture of Toledo with a note that it was taken there. Yet it was so many years ago I could have made a mistake. So not sure! 🙂

  5. So true… many places are over run by other tourists like you who want to see it all. Off season travel seems to be better or finding a few hidden jems. I, like you, enjoy getting lost sometimes. I loved Spain… I didn’t get to Toledo, we opted for Segovia for the castle, but was in awe of the aqueduct!

  6. You should come back again to visit my city! I hope this time you will enjoy the best! Toledo deserves a second oportunity 🙂 Best regards.

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