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Please help with trip planning to Spain next September/October

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Hi

My husband and I are native New Yorkers in our mid-sixties, still working. We would like to travel to Spain for about 12 or 13 nights. I visited Madrid on a European trip many years ago. I would only like to return to Madrid to see The Prado again and perhaps go to Toledo. My husband may want to still see something of Madrid. I want to focus on wonderful, atmospheric smaller cities/towns for art, food, wandering on charming streets and squares. I think Audulucia fits the bill. We will not be renting a car. My questions are: should I start in Madrid briefly?; would it help to go on some organized tours and/or use a private guide to get oriented and see things we couldn't do without a car?; how should we travel between cities and towns? I am concerned about moving around too much with luggage. Also, we want to end the trip with being somewhere in Andulusia that could be relaxing, not overwhelming but still interesting. Is it worth going to any seaside town, including Malaga? What difference does it make if we go in September vs. October?

Any advice would be greatly appreciated! Much thanks!

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