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Travel to Spain: Madrid & San Sebastian

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I'm planning to visit Spain in April or May 2013 and would appreciate any information on a 8 to 10 day itinerary. I'm interested in visiting the Basque region as well as a city in Spain, mainly Madrid or Barcelona. Which region should I begin at, can I do all three cities in 10 days? I would also welcome suggestions on places to visit, including entertainment as well as the best way to connect to each location. Is travelling by car a good option, etc.? Thanks in advance for your help!

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