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Madrid--Day trips out of the city

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Hi all! We are leaving in 2 1/2 weeks for Spain. Visiting friends in Madrid but we will have lots of time on our own and I don't want them to feel obligated to take us out of the city touring. Would like to do Toledo and Segovia day tours. Have been told we can take a train directly, but where exactly will that leave us? Is that not a really smart idea when there is so much to see and do once we get there by train? Are we going to have to trek a bunch to get to where we are going? Should we book a tour, and if so, we would only be interested in a tour that was very informative on history/culture and not just to shuffle us about. We are traveling with our almost 14 and 12 year olds. Thanks!!

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