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Basque and Catalonia Road Trip

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Hello!
My husband and I will be going on a 19 day trip to Spain in September. We are flying into Madrid because we got a great flight deal, but do not want to spend a large amount of time there. We are most interested in the Basque region and Catalonia and want to spend a good amount of time in and around Barcelona (at least 5-6 days). We are wanting to rent a car and leave from Madrid to go north with Bilbao as our first destination, then onto San Sebastian. We would also stop in Pamplona and then onto Barcelona with a side trip to Cadaques and Figueres. We will probably return the rental car once we reach Barcelona and fly one way back to Madrid before our flight home, unless it makes a lot more sense for cost reasons to drive back to Madrid to return the car, but I have heard that Barcelona will be difficult with a rental car.
A little about us... we are foodies and we love any art and cultural events. We also both are amateur photographers but love inspiration from our travels so we would love to know about scenic locations that can't be missed.

Our questions:
1) What can we not miss in between all of these major stops?
2) Should we go into French Basque Country from San Sebastian? (is this allowed with a rental car?)3) How much time would you allocate for each area?
4) Should we dedicate 1-2 days for Madrid or will this make our timeline too tight?

Thank you in advance!

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