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Travel from Madrid, San Sebastian and Barcelona

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I am traveling with my two teenage sons to Madrid in June. I would like to spend a couple of days in Madrid, then go to Barcelona and San Sebastian. Can anyone recommend if I should fly, take the train or rent a car between those cities? If we rent a car, suggestions on places to stop along the way? Is it easy to naviagate? We are only there for 8 days, so I would like to spend 2-3 days in each place - it is also my sons 18th birthday - so a recommendation for a special place for dinner would be great!
Thank you!!

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