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Flying into Madrid and out of Paris. Any input is greatly appreciated!

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I am in the he midst of planning a 14 day trip to: Madrid, Barcelona, San Sebastian, Bordeaux, and Paris.
I am so excited about this trip and would greatly appreciate all your input to make it an unforgettable one.
So far, I put the following itinerary together. Again any input is greatly appreciated, including recommendations for scenic sites, restaurants and hotels. Thanks!
Itinerary: Flight from Chicago into Madrid and out of Paris
• Madrid (3 nights with a possible day trip to Toledo (train 0h33))
• Madrid – Barcelona (train 2h38)
• Barcelona (2 nights)
• Barcelona - San Sebastian (train 5h45)
• San Sebastian (2 nights)
• San Sebastian – Bordeaux (train 2h55)
• Bordeaux (2 nights)
• Bordeaux – Paris (train 5h34)
• Paris (4 nights)

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