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Requesting help with Spain Itin - Couple with 12 YO

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In late March, we are traveling to Spain with our 12 year old girl. We are flying in and out of Madrid and will have approximately 10 days in Spain but need to spend at least 1 night each in Toledo/Madrid & Seville. We've already been to Barcelona, Bilboa & San Sebastian so don't plan to re-visit on this trip. We plan to stay on the Western & South side of Madrid but are wide open to places/activities. We enjoy (maybe equally): Food/Wine, Art, Outdoor activities and taking trains.

I'm asking for help on a couple of topics:
1 - is it worth spending a day or 2 in Lisbon/Portugal as none of us has every been?
2 - Are we better off taking trains btw cities or just renting a car?
3 - Is Caceres worth a stop (I hear the food is phenomenal)?
4 - Any thoughts on hotels/restaurants would be greatly appreciated!

Thanks in advance!

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