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Trip to Italy and Spain

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I would like some input on a trip we are planning to Italy and Spain this fall. We are flying into Milan on Sept. 26 and arrive at 8:30 am. We are flying out of Madrid on Oct. 16 at 1 pm. Tickets are already purchased as those are the airports I could find with our miles on American. The reason we are combining the two countries on this visit is because my nephew and his wife are in Aviano,Italy (45 min, north of Venice airport) and our son is doing a semester exchange at the Spain Air Force Academy in San Javier, Murcia, Spain (which is south of Valencia which is south of Barcelona) Also, now our daughter and son-in-law are going to join us on this trip. They will be on their way to start new teaching jobs in Surat Thani, Thailand. They plan to fly into Venice about a week before us, stash their extra Thailand lugguage at my nephew's and visit Venice and north to Cortina and maybe into Austria some.

My nephew and his wife have been stationed in Italy for 3 years now, so they have been all over Italy and much of Europe. However, when we asked them where in Italy that they might want to go again, they said Cinque Terre. So they are going to drive, with our daughter and son-in-law to Cinque Terre on the day we arrive in Milan (they were going to pick my husband and I up at the Milan airport but both of their vehicles only hold 5 people so all 6 of us traveling with them became impossible when our daughter and her husband decided to go to Thailand via Europe). Anyway, my husband and I intend to take the train from the aiport to Milan Centrale and then train on to Cinque Terra where we will meet up with the other 4.

We plan to stay 2 nights in Cinque Terra. From then, we are considering getting a rent car when we leave Cinque Terra and going to an agriturismo near Montepulciano for 5-7 nights and but haven't decided for sure on that. We may try to figure out something for Friday and Saturday nights to still doing something somewhere with my nephew and his wife before we head down to Montepulciano. Any suggestions?

After that we thought we would return the rent car, go to Rome for 2 nights, and then fly to somewhere in Spain for 7 nights before returning to Madrid the night before our flight back to the States. I was thinking about flying from Rome into Barcelona for a couple of nights then renting a car to go to southern Spain to hopefully connect up with our son on the weekend somehow but that may be too much in only 7 nights.

However, the Spain part is wide open at this point, as it pretty much the Italy part besides the first 2 nights in Cinque Terre. Any suggestions from previous travelers would be most appreciated. I already know that 3 weeks doing 2 countries is not enough time. But it is what we have, and since we definitely want to go to Italy and then want to see our son in Spain, it is what we have to work with.

We all really like the outdoors, we like getting to know the culture and people, we like walking tours and audio tours and architecture but are not big museum goers. If possible, we would rather stay in apartments or small B&B's or small family-owned lodging (not big hotels). We are also not the type that tries to check off a list of places we have been by only spending a few hours in a place.

Thanks ahead for any advice :-)

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