Itinerary Review

Looks nice, but you have not shared how you will travel. If public transit, just check the schedules to see if this order is ideal. I see no red flags. I would add the extra nights around the halfway point, so you have time to do laundry and such. You also likely need ot be in Madrid the last night before your flight out, so you could put all the time in Madrid together at the end--Madrid to Cordoba or Toledo is a short train trip and not too difficult to do on arrival.

I am leaning towards public transportation. That's a great suggestion to group Madrid at the end. Thanks!

Sounds good then, all of those places are well linked by train. Here is the train link if you need it: https://www.renfe.com/es/en

Bus is an option for some of these routes also. I used the Rough Guide, which was a helpful guide. This website is good too: https://www.andalucia.com/travel/bus/home.htm

You might add one night to Ronda so you'll have a full day there. Don't miss the sunset over the gorge!

I'd just urge you to consider the pace of that trip with your family. Everyone and every family is different, but this 12-night itinerary has 6 episodes of packing up, checking out, moving on. That's a whole lot of work, even for families with abnormally cooperative tweens.

You'll see a lot, but at what level of effort and stress?

Madrid, Granada and Barcelona are very important cities and they alone are worthy of your whole time allotted.. I'd add one day to Madrid and take the train 40 miles down to Toledo for a day trip.
The logistics of moving so many people from place to place puts undue pressure on The Dad. It's difficult enough just trying to entertain the 3 kids at their age. It's also difficult to keep'em out of their notebooks/smart phones.

Focussing on one region is sensible.

Two nights somewhere is only one full day there, so you are going to be spending quite a proportion of time in transit, packing and unpacking compared to actually seeing places. Seville can easily fill three whole days. One night stops are tiring. I suggest that you consider minimum stays of 3 nights.

Good points. That was part of my reasoning behind keeping the extra three nights in my pocket. We camp a lot and my kids are use to packing up gear and moving to different camp sites but I can see where 1 night stops might be too stressful. I want to keep the smaller towns/cities because I think my family will like those, maybe even better than the larger cities. I do think I will add extra days to those stops. Thanks again.

I think strategic use of the extra three days will help. I like to stay at least four nights at some point in a trip even not shepherding adolescents around.
Poor Toledo--everyone always says it's nice to stay overnight because all of the day trippers, but having to transit through Madrid by train does kind of make it complicated!

I would add an extra night to Seville. There is so much to see and do in Seville, so with 4 nights you will have 3 full days. Also a more relaxing pace.

Because you are a family of 5, perhaps spend 2 nights in Toledo instead of one so you don't feel you are rushing around.

For your extra 3rd night, perhaps add it to Ronda to eliminate the one-nighters, or add it to Madrid so you have a more leisurely pace in Madrid.

May is a perfect time to visit Andalusia! This is a very hot region during the summer months so good for you that you are able to travel in May.

Is it possible to purchase open-jaw or multi-city tickets so you don't have to backtrack? For example, fly into Madrid and out of Seville. You would then have to re-arrange your current itinerary.

Recommend you book your flight through Madrid with same day connecting flight to Granada. Doing so is an efficient manner of travel as you will utilize the same mode of transport. We purchase tickets from Miami to Granada with a connection in Madrid. We choose to fly Iberia and the connecting flight is seamless. We travel only with carry on luggage making the transition to the connecting flight easy. So our "day" is an overnight flight arriving early morning in Madrid, two hour connecting time and less than two hours arriving in Granada noonish. Leveraging the same travel mode reduces stress, time consumed and (we find) overall expense.
Check out water parks in Granada, Seville and Madrid as they provide a welcome relief from heat and travel stress for all ages.
Madrid offers several wonderful parks with Retireo being most convenient and provides excellent place for family picnic.
Focus on creating itinerary providing best opportunity to create wonderful memories of "being" instead of "seeing". Doing so requires a commitment of "slow down, you move too fast, you got to make the moment last."
Take food risks as eating tapas means a $4 investment with attempting food you may never get to again attempt. Love it or hate it, the expense is minimal and the potential reward great. Sometimes the worst taste bud experience can create a cherished family memory.
Hydrate and stay hydrated as recovery from dehydration takes a minimum of a day. Public water is good water do no need to constantly be purchasing bottled water.
Regardless of the selected destinations your investment into this family journey shall have long lasting positive returns!

Not a bad plan, however, I recommend

Spend one day on a day trip from Madrid to Segovia.
Don't need 3 days in Granada. Add one more to either Madrid or Seville.

Why not take a direct train from Seville to Cordoba (45-minutes) for the day instead of spending the night in Cordoba.

So it sounds like you haven't been to Europe as a family. Please stop to consider -

• You can only move as fast as the slowest person in the group (and that isn't always the same person - the sleepy-head, the window-shopper, the breakfast dawdler . . . . .
• packing/unpacking is time-consuming unless everyone is experienced and efficient
• It takes time to get oriented to each new place, find your bearings, learn where the street names are, how to use public transportation, etc.
• Travel time isn't just the 2 hour train ride, it's getting packed and out the door to the train station, then from the train station to your next hotel to check in and unpack. If you travel in the morning, you use/lose about 1/2 day and you have to drop your luggage at your hotel and probalby can't get into your room/s till later.

For those reasons, I would eliminate Ronda - it's too much of a schlep for a 1-nighter. And it's really not that spectacular. The kids might really like a day trip from Sevilla to Jerez for a horse show at the Royal Equestrian School. I believe if you get there well before the show begins you can see the horses in the paddocks. Consider 2 nights in Toledo, arriving late in the day and leaving early so you have one full day there.

The Naval Museum in Madrid is very interesting, even though there's not a lot of English explanations - take passports with for entry. It's mostly about the golden age of Spanish exploration.

I've looked at the above comments, and would add:
I would go with public transportation. Spain has a great train system.
You have resisted hopping all over the country, but you'll still be hopping. I would recommend against adding more destinations. Some of the above comments recommend Segovia and Jerez de la Frontera -- both would be great places to visit, but I don't think you can squeeze them in without becoming too rushed. I realize there's a conflict between wanting to "see everything" (which you won't succeed in doing anyway), and getting to know what you do see at a pleasant pace. If the latter is more important to you (and it may not be), I would recommend spreading those three extra nights among Madrid, Cordoba, and Seville or Granada.