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Toledo, Segovia, San Sebastian - route planning advice?

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We'd like to go to the following cities (starting out from Madrid):

San Sebastian
and maybe even Santander

What route do you suggest? Should we rent a car or take trains and buses? Can we fit all of this into 4-5 days? (I know it's not ideal, but this will be after an 11-day tour, and 4-5 days is all we've got afer).

My plan is to go to Toledo by bus (sleep there), then go to Segovia (train or bus), and then rent a car in Segovia and take 2 or 3 days to go to San Sebastian and return to Madrid. I've never been to Spain, so I don't know if this is feasible or too rushed. Also maybe the train would be better to San Sebastian??

Any advice appreciated.
By the way, this will be in early October. We won't have any reservations, so we'll be completely flexible.

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