Starting to Doubt Myself - Is Toledo Worth a Possible Day Trip?

Really, your trip looks fine. I too prefer 3+ nights and you will enjoy it as it is.

If you really wanted, you could drop Cordoba to 2 nights without missing a lot, it's not my favorite (but I still like it a lot). That way Madrid could be 2 nights, 1 day of which is spent in Toledo. Toledo is very important historically - and is beautiful. But you can't go everywhere and really, you have a great plan. Two 2 night trips at the end might not be ideal for you, too.

Your family member is mistaken. There is certainly enough to occupy two to three days in Cordoba. Admittedly we are slow paced tourists, but if you cover the city faster, there is also a morning trip to the highly recommended Madinat al-Zahra which is just outside the city (I think the tourist office run a bus service).

Toledo is very nice too, of course, but I'd save it for your next visit when you could stay over for a couple of nights.

Well, my general feeling is that once you have planned to this extent, resist any urge to start tampering, or the whole house of cards comes tumbling down. Yes, Toledo is great, better as an overnight than with the daytrip crowds, but so are a dozen or more locations you have not mentioned, you just have to limit to what is in your scope.

My only concern would be the one night in Madrid, by the time you get up, travel to Madrid, get settled, a good chunk of a day is gone, then repack for the flight, and likely an early flight the next night, leaves nothing for Madrid.

If anything, I would suggest cutting Cordoba to two nights, catch a mid-day to later train to Madrid, settle in, then have a relatively relaxing last day, followed by a great last night meal. While Madrid may not interest you, it is a great town, and probably one of the better food cities I have been to...different than the Southern Spain cuisine you will be having and some examples of things from many regions (Galicia, the Basque region, etc.)

I spent two nights in Cordoba and 2 nights in Toledo. They were my favorite places in Spain. I found 2 days in Cordoba were adequate and I did it slowely with a gimpy foot (so more rest time). It certsinly needs more than a day trip, however.
I really liked Toledo, however, I wasn't travelling with 3 generations of people. If anyone likes el Greco, this is where you want to see it, particularly hanging in situ as Rick likes to call it.
I have a suggestion, depending on your flight, why not overnight in Toledo for 2 nights instead of Madrid and just go in for the flight?
I travelled from Cordova to Toledo and arrived there about 2 pm as I was not sure I could make the the earlier connection.
Otherwise, stick with your plan and give Toledo more time when you return to Madrid.

OMGosh, I thought Cordoba was fabulous! I would wonder about the interests of the person who felt it wasn't worth much time. Think about whether your interests align with your friend. I also enjoyed Toledo very much, as well. I stayed one night in Toledo and I completely agree that you get a whole different feel of the city when the day trippers are gone. Same with Cordoba. I agree that in comparison to the other cities, Madrid would rank pretty low in terms of history or culture. I get that you like longer stays, however if you could handle a one or perhaps two night stay, I'd stay over in Toledo. In my opinion, you could take a night away from Ronda, Cordoba or Granada. On the other hand, I agree with the comment, that once you have set an itinerary and feel happy with it, avoid the temptation to change it based on other people's comments. You've done a lot of research and you know best what you like, make a plan and stick with it unless you really determine that the plan is fundamentally wrong. You do have a great trip planned and no matter how you work it, you won't be able to see everything.

I strongly disagree with your relative as well. We loved Cordoba!!! it was one of our favorite places. We stayed 2 nights but could have used a 3rd night. The Mezquita is magnificent; however, there is more to Cordoba than just the Mezquita. We enjoyed the Alcazar gardens, Roman Bridge, wandering around the Juderia, and the Palacio de Viana (a hidden gem). Cordoba is gorgeous and romantic at night. The Juderia is beautiful with white washed buildings, flower pots all over, gorgeous patios, etc. I believe the Patio Festival is in May, so you might be there at the right time to see the festival.

I also agree that Toledo is best seen as an overnight or two. We stayed one night in Toledo, and if we hadn't, I think I would have left there feeling "what is all the fuss about?". It's a gorgeous city but over run with tourists and tour buses during the day. At night it is peaceful, quiet, mostly locals, and beautifully lit up.

I think I agree with posters who have suggested leaving your itinerary the way it is. I, too, had a relative who told me Cordoba is not worth much time at all when we were planning our trip, but luckily I didn't listen to her. I think people who don't like Cordoba as much only stop there on their way to Seville for a few hours to see the Mezquita. So they really haven't seen the city at all.

I agree with Paul that Cordoba for two nights is sufficient and you should stay two nights in Madrid.

Thank you all so much for your incredibly helpful replies. I read them to my family last night.

We have decided to keep it simple and as is. We may choose to cut one night from Cordoba and add a night to Madrid, but are not sure about that yet. Our thoughts, for this trip anyway, was to arrive to Madrid in the afternoon or whatever, check-in to our hotel, go somewhere to eat, and fly out the next day. It would have been lovely to have just a few more nights, but we can't change any of that. Paul, your comment about not tampering and the house of cards tumbling down, that is so true. Once I read that to everyone, our mind was pretty much set to keep it all is.
Jules, you are so right. We can't possibly see everything.

We do hope to visit Spain again, to see Madrid, Toledo, and other parts, but we don't know when that will be. There are so many places throughout Europe that we would love to return to and others that we still have not seen. I know that you can all relate to that!

Again, thank you all so much for helping us in this decision-making process. I cannot even begin to tell you how much I appreciate you taking the time to write such helpful replies.

Gee, you made a decision before I got to weigh in. But since nothing's set in stone, here's my opinion.

Cordoba is my favorite Spanish city. On each of my 3 visits, I've returned to the Mezquita and roamed the Juderia. Other than that, I've found new sights to enjoy and new places to wander every time. That being said, Toledo is also great. I would consider dropping a night from Sevilla and even one from Cordoba for 2 nights in Toledo. What time is your flight out of Madrid? You may be able to get to the airport in time from Toledo and not have to stay in Madrid overnight. If not, maybe take just one night from Sevilla for one night in Toledo. What made it easier for me to visit Toledo was to take a small overnight bag and leave the rest of my luggage in the Madrid train station.

I know you have 'all' decided, but afterwards I thought about your comments about 'so many places to return to'....so how old is FIL? Has he got a lot of travel life left in him? Is he just going along for the ride and more family time? Maybe ask how much he wants to see Toledo.....he is the most one most likely to have fewer travel choices as time goes on....

I cannot even begin to say how thankful I am to you all. Thank you for taking the time, as always, to write such helpful replies and patiently deal with my indecisiveness and all my questions.

Chani, we seriously considered dropping a night or two from Sevilla or Cordoba, and to spend those two nights in Toledo or Madrid. We read your reply together last night. Our problem is that our flight out of Madrid leaves at 10 AM or so. It was meant to leave in the early afternoon, but they just changed it. With a bit of reluctance, we figured that we'll focus on Madrid, Toledo, and other places in a future trip. It's so hard for me to make these decisions. I struggled like this with our 2017 trip to France, and our 2018 trip to Italy. All three countries seem to have so much to do and so many places to visit. I always enjoy your posts. Did I ever tell you that Israel is one of my favorite countries in the world?

Maria, thank you also. FIL is 75, but an incredibly healthy and fit 75. He goes mountain climbing in California almost every weekend. He's flexible and the best travel partner ever. He lets us make all the decisions and goes along with the flow.

Once again, thank you everyone.