This summer, instead of spending my vacation traveling home to Canada, I am planning to spend it in Spain. I will meet up with friends in Barcelona and Costa Brava (I have no choice in these locations), but after that, would like to spend 10 days traveling and possibly depart Spain from Bilbao. (I haven't book this portion of airfare yet.)
Living/working in the Middle East and spending short breaks in Turkey, I am less interested in Islamic history and mosques than in Western art, architecture and food (that I can't get in Iraq-pork, seafood, good cheeses, nice wines, etc). From Barcelona, would it be feasible to visit all of the following: Madrid (is Toledo worth a day trip or would I need longer?), Segovia (and/or Salamanca?), San Sebastian and Bilbao... and although I am afraid to drive, I would LOVE to spend a day visiting such bodegas in Rioja as Ysios (I read this is one of the few open in August). As I have never been to Spain, I am also open to other suggestions...
And finally, I wonder if it is a good idea to purchase a Spanish rail pass or are there better/more cost effective ways to travel in these 10 days. (And if one has a pass, is it easy to obtain tickets on desired trains in August or do you have to book well in advance).