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!
Travel to Spain: Madrid & San Sebastian
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If you want to pick 2, then my vote goes to Barcelona and Madrid or you could start in BCN, go to SSebast. and finish with a short stay in Madrid. We always travel by train so no opinion on car, except even in SSebas. parking might be difficult - NO WAY I'd have a car in the other cities.
We recently spend 3 nights in San Sebastian, really really liked it but the weather can be challenging (we were there near the end of May). I think it would be a very nice region to drive around but if you do want to rent a car, maybe you want to stay outside San Sebastian or make sure your hotel has a parking option.
"can I do all three cities in 10 days?"
That depends on what you mean by "do". It also highlights the difference between what is feasible (yes, it is feasible) and what is enjoyable.
Madrid and Barcelona.
I was happy to see that you are already planning your trip as the planning is half the fun ,well maybe almost half.
I was in Madrid and San Sebastian from the end of May 2012 to mid June.
We drove from Madrid to San Sebastian stopping a night in the beautiful city of Burgos. It is a 5 + hour drive to San Sebastian, a long haul from Madrid. Friends who had visited San Sebastian in May found it more deserted on the beach due to the cooler weather. We were there nearer the middle of June. We go for the wonderful Pintxos crawls. The offerings found in the Basque region are the best in Spain. With a car you have the freedom of driving to Hondarriba or over the border into France, perhaps Saint Jean de Luz, both cute places.
Barcelona or Madrid . First I know my son in law found driving in Madrid a real challenge. so many no left turn streets. Definitely more a Metro or walking city. This time I picked Madrid but I would go back to Barcelona in a heartbeat. Definitely a hard call.