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3 weeks to spend in Spain, Italy, that enough time?

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My husband and I have only one trip (Scotland) under our belts outside the US so are relatively inexperienced in overseas travel. We are physically active and love outdoor activities of all kinds (running, biking, hiking, fishing, kayaking, etc). We also love experiencing the history, foods and beverages of an area.

We are in the very beginning stages of planning a 3 week trip sometime in 2015 and would ideally like to visit all three countries mentioned. We are most interested in places off the beaten path. We prefer the natural wonders of an area and places the locals like to go to versus the typical tourist attractions. We would consider spending some time in a few of the bigger cities if there is something that just shouldn't be missed.

Is it possible to have a fairly relaxed time in only three weeks? Can it all be done by train and public transportation or would it be best to rent a car? Is it best to do fly in/out of the same airport or does it not make that much of a difference in airfare cost?

I'm sure I will be posting more questions as things progress so any other advice would be appreciated.

Thank you,

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