What is the best way to see Toledo?

A couple years ago my husband and I took the "cheesy" train ride. We enjoyed it because it takes you around town a bit, giving you nice views of the surrounding countryside and then it goes around the perimeter of Toledo, giving you nice views of the town itself. I don't recall it taking very long and, especially since you have limited time, I would recommend it for giving a nice overview. I can't compare it to the city bus, however, as we didn't take the latter. As an aside, we've seen quite a few cathedrals in Europe but the one in Toledo was extraordinary. Highly, highly recommend a visit inside.

I did a day trip to toledo and did the cheesy train and i liked it. It went around the outer edge of town and stopped at a viewing point so you could see the whole town and take pictures. Get to the left side! Most picture shots are from the left. The rest of the town is easy enough for walking. The cathederal is beautiful.

Thanks for the advice! I think we will start with the train and then go by foot.

Since you asked What is the best way to see Toledo? I've got to suggest that seeing Toledo as a day trip is NOT the best way. In fact, it's probably the worst way. Everybody does Toledo as a day trip, and guess what? From around 10 am to around 4 pm, the place is completely mobbed. Outside of those hours, it's empty, and wonderful. I had family members with limited European travel experience who were planning a short trip to Spain this past spring. I urged them to spend the night in Toledo rather than doing the obvious day trip along with 40,000 strangers who they would be shoulder-to-shoulder with. They ignored my advice, because they said it would be more convenient as an easy day trip. After they got back, I asked them how they liked their trip. "Mostly it was pretty good" they said. Did you go to Toledo?, I asked. How did you like it? "Oh, we hated Toledo - it was so crowded, it was really awful!" Seriously, don't do it as a day trip. Take the train from Madrid, arrive early/mid afternoon so you can appreciate how much better your experience will be: you'll get there in time to see the streets packed with crowds, then you'll watch them all drain out of the city by 4 pm, leaving it to you and a few other smart travelers. Enjoy the later afternoon and evening, with empty streets and photos without 500 people in front of what you're trying to see. Have a nice meal, wander the silent streets, and sleep in the old center. Get up early, enjoy the beautiful old city as if it was yours, and around 9:30 watch as the tour buses roll in by the dozens, disgorging thousands of daytrippers. That's your cue to get back on the train for Madrid. You'll get to spend about the same amount of time as the day-trippers, but your experience will be completely different.

Unfortunately our plans are already set and we can't spend a night in Toledo. We do want to spend the evening there, since Madrid is just a quick train ride home. Is 4pm the latest the trains leave? Because we were planning on the leaving the city around 9pm.

I agree with David but understand that you have a set itinerary. If the train schedule doesn't work out check the bus schedule - it's also a good way to get to Toledo from Madrid.

Train schedules - www.renfe.com - last from Toledo at 2130

We liked just walking around, especially late afternoon and into the evening. Toledo was our favorite medieval "twisty streets" location in Spain.

Thanks everyone for your input. I'm hoping we will get to see the non-touristy side of Toledo in the evening since we don't plan on leaving until the last train leaves. Rick suggests buying our train ticket a day or two before in order to make sure seats aren't sold out. If I'm set on the day we are visiting Toledo can I just buy a few months in advance?

We just did this in July. We took a train from Madrid at around 11 AM. We got to Toledo and got oriented while having lunch. We wandered around a bit and found the cathedral. Wow! What an edifice! We walked around some more and toured more sights and finally took the cheesy tourist train around 5:30. This was a narrated tour that takes you across the river to some high ground for really great views of toledo. We stopped for photos and then completed the tour. Afterward, we had dinner and wandered the streets more. The crowds didn't really thin out until after 6 on the day we were there. We took the last train back to Madrid. If you are doing a day trip, I recommend staying as late as possible.

Just there last week and wanted to highlight something Rick suggested in Toledo.... El Trebol restaurant-short block away Plaza de Zocodover at end of a street.
Tucked away but really cheap and good. We had tapas for dinner and then went back for breakfast and drinks next day. 8.50 euros for JUG of Sangria :)! It was an incredible value but a little tricky to find as it looks like the road ends...

@Michelle, you had me at Sangria! hehe. Thanks for suggestion, we're going to try this place.

I spent a week in Toledo a few years ago and it was remarkable. You mentioned getting off the beaten track. If you like El Greco, I'd suggest a visit to the convent of Santo Domingo el Antiguo. Check the hours carefully; it's a cloistered convent. The altarpieces at that convent was the commission that brought el Greco to Toledo, and it's where he was originally buried. Although some of the originals are now in the Prado, there are excellent reproductions in place for the missing pieces, and it is wonderful to see the paintings as he intended them to be displayed. It gave me a whole different impression of a couple of the pieces. It was also a very pleasant walk to get there from the cathedral, and returning by a different route was an opportunity to explore other areas.

I have no doubt that, time permitting, a night in Toledo should be strongly considered. But if the choices are taking a day tour from Madrid to Toledo and not seeing Toledo, my guess is that the former is the better choice. I am hoping to go to Spain next April. We will be flying into Madrid, arriving early on Wednesday, and leaving on Saturday for Seville. That is the time we have. We intend to take a day tour of Toledo on Friday. Given the inconvenience of carrying bags and checking into another hotel for one night, and with the major sites in Toledo closed at night, a day trip seems to make more sense. Venice is mobbed during the day but empty at night. But I have enjoyed every minute in Venice, whether during the day or at night.

I'm usually not one for things like the train tour, but we actually really enjoyed it. However, I recommended doing it at the end of your stay, rather than the beginning. It doesn't really get you oriented to the city because it largely drives outside the city for views. If you do it at the end, it is fun to identify the places you have been and see the city differently. I agree that an overnight is best (we spent three nights and two full days), but a day trip is still worthwhile.

I am also planning a day trip to Toledo next month. I was also not too excited about the "cheesy train" and felt like I needed more than what I was finding in the RS book. I found these very interesting self-guided walking tours from a Google search and plan to do them. They seem to be well laid out and begin on the side of town of the bus/train station. Like I said, I have not done them yet, but plan to. I hope this helps!!
http://www.go-toledo.com/maps/

More a question than a reply, but on the same topic: We'll be in Spain in January and wonder if even then Toledo will be mobbed. If so, I'll plan an overnight trip; if not, I'll opt for a day trip rather than change lodging for one night. (We'll be in Madrid, Sevilla and Granada.)

Marcia, the crowds will certainly be a lot thinner in January than at peak times, so go ahead and do a day trip if that works best for you. Honestly I was there in early October a few years ago and don't remember it being particularly crowded. Of course, be prepared for cold temps in Jan. (30's and 40's).