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Towns or stops between Gibraltar and Malaga

Have enjoyed getting a lot of info from searching the different Spain topics for our upcoming trip. I know Gibraltar is not high on the list for many, but will be near there and my son loves WW2 history so worth it for us to spend part of a day there. But would rather not stay for a full day or make an overnight of it. If leaving mid-afternoon and heading towards Malaga are there any other towns or stops that would be worth making on the drive (we will have our own car)? Castellar de la Frontera or maybe dinner in Sotogrande (Cancha II Asador or Casabon Sotogrande maybe)? Museums, historical sights, or just nice views and architecture are all great. Just something to tack on to a road trip.

Thanks.

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