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Madrid Day trips - Segovia and Toledo

We are a group of six staying in Madrid for several days. We plan to take two separate day trips (to Toledo one day and Segovia another). If we take the train to one or both is it easy to get an uber once we are in town if we want to see something that is too far to walk? Or is renting a car/van a better choice? Is parking an issue in either town? We will be there in late October.

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