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Visiting El Escorial, Segovia and Toledo??

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Hello - Hubby and I are spending 5 full days (arriving on Tuesday, Oct 8th, and flying out on Monday, Oct 14th) in Madrid and are trying to plan our time. 2 Questions - 1. If we rent a car can we visit El Escorial and Segovia in a single day? 2. Should we rent a car to visit Toledo? Or, is it really easier to travel via the high speed AVE train? And if we travel by train to Toledo, do we need to make advance reservations given that we are traveling in early October? Thanks for your suggestions!

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