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Need you help and input to build an itinerary to Spain and France

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Hi!
I just started looking into planning a trip to Spain and France (approximately 10 - 14 days) sometime in September (assuming the weather will be nice/ temperature in the mid to high 70s).

I wish to fly from Chicago to a major city in Spain (perhaps centrally located) and preferably use the train system or if necessary rent a car to visit a few other major popular cities; as well as, if possible, visit small recommended towns on the way.

Eventually, I wish to take the train from Spain to France stopping at the most notable towns/cities on the way to Paris where I plan to spend a few days before returning to the states. Any and all recommendations are welcome.

I enjoy adventuring different cities, learn about different cultures and history, site seeing, wine tasting, and absolutely dinning. I appreciate the small local shops or what they call (hole in the wall) restaurants where I can mingle with the locals and enjoy a home cooked meal.

I am so looking forward to your response and thank you in advance for your input.

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