Cadiz to Malaga and In Between

You've overlooked Cordoba. It would fit between Toledo and Seville or between Granada and Madrid.

Others will know more about public transportation options since I always get a rental car. That stretch of coast is my least favorite since the entire Costa Del Sol area is overbuilt. If you like beaches then it might work for you, but we don’t go to Spain to hang out on beaches. For strictly lodging any place in the Marbella area would work. There are no big cities between Cádiz and Malaga and there is very little to do in La Línea de Concepción. It wouldn’t be my choice. Maybe consider staying on Gibraltar itself if it’s a must see. There are more shops and restaurants than in La Línea.

If you had a rental car and didn’t take the coastal route, from Cádiz you could head over to Jerez de la Frontera, then up to Arcos de la Frontera. From it you could drive to Ronda possibly stopping at a white village or two, then work your way back down to Málaga.

You should add a day trip to Segovia from Madrid.
Toledo 5 days, what are you going to do for five days, that is way too much.
Cordoba is between Madrid and Seville, add a day for that city.
Still can't see spending so much time at other cities you have listed like Malaga 5 nights and Granada a week!
Madrid a total of 10 days.

What sites have you researched that you plan to see with so many days in many of these cities.

You won't want a car in the cities, so yes, take the trains.

Between Cadiz and Malaga you could add in one of the white villages like Ronda for a few days. There are buses from Seville to Ronda and bus or train from Ronda to Malaga.

We are going to Andalucia and then Extremadura on our trip (Feb/March 2023) but are doing it in this order -

• Cordoba 3 nights
• Malaga 4 nights (day trip to Granada for Alhambra)
• Seville 6 nights (day trip to Cadiz)
• Caceres 3 nights
• Salamanca 2 nights
• Madrid 5 nights.

We are travelling by train and bus and this order works out well in terms of length of train/bus trips between cities. We are 59 and 73.

I used the Trainline website/app for train/bus planning as it will show you both your train and bus options over the same routes.

I would look at rearranging the order of your itinerary to avoid backtracking. something like this:
Madrid- Toledo- Caceres- Sevilla- Cadiz- Tarifa- Malaga-Granada- Cordoba(too good to miss)-Madrid. Keeps you moving without doubling back. Number of days is up to you Toledo is great but not 5 days great, likewise Granada. You've got a lot of time to work with I'm jealous.

Thank you to everyone that replied. I’m now looking into a rental car for one week, Cadiz to Malaga. That way we’ll more easily be able to get to the white villages and Gibraltar. Also, looking at working Cordoba into the itinerary.
Happy Travels!

You could also add a visit to Jerez de La Frontera. You could do a day trip from Seville or Cadiz or stay the night. It's a lovely town, a little less crowded with tourists and the speciality is Sherry (Jerez) so there are lots of bodegas with sherry tours and tastings and its a great place to see Flamenco.

You should definitely visit Cordoba, and try to spend 2 or 3 nights there. Since this is a long trip, it doesn't make sense to visit Cordoba as a day trip. You don't need 5 nights in Toledo and you don't need 7 nights in Granada. I would take 1 or 2 nights from each of those places so that you can include Cordoba in your itinerary.