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3 day-trips from Madrid using the train

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Hi, Fodorers:

Planning our late-August trip to Spain, we have net 4.5 days in Madrid, after 4.5 days in Barcelona and 2 in Girona. Of those 4.5 Madrid days we want to spend 3 days on day-trips outside, using the train, and we even found accommodation very close to the Atocha station to make it easier for us.

2 questions:
1. We need to choose 3 destinations (different enough in style or atmosphere) out of this list: Toledo, Segovia, Cuenca, Avila or Salamanca.
2. Does it make sense to do an online purchase of a train-pass for a couple for those 3 round-trips, so that we're free with our itinerary and can jump on a train in the last minute?

Thanks!

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