Which villages near Lisbon, Porto, Coimbra should we check out?

Seasoned, Daring and black - That's how I'd liked to be seen. I'm on my way with my blonde wife in tow towards a new adventure. She won't take to kindly to the notion of "in tow" - it's meant in a poetic sense rather than dominance. We are on our way to Portugal after a three month search of possible retirement locations across the world.

We're coming to Portugal for our first visit beginning the last week of November (Our Thanksgiving Holiday) and we plan to stay for no more than two weeks, maybe less if we become disappointed or convinced. All the following background chatter is to inform this question - which villages near Lisbon, Porto, Coimbra should we check out? If you feel so inclined write a few words as to why?
---
We started our quest by deciding that we would no longer stay in our current home (5,000 sq. ft. house on three floors 45 miles from Chicago) - to far away from the City to take advantage of the culture, to conservative to be happy with our neighbors, to early (and limited) to take advantage of the just passed marijuana legislation in Illinois ,and finally we are both sick of shoveling snow.

So with these goals in mind we began our search, not stuck to any destination, we looked at Asia (Vietnam, Malaysia and the Philippians) , to far for our grandkids to visit and the politics seem way to shaky for our taste. We considered other parts of the USA (starting with - Washington State and Colorado, the new marijuana are very interesting- stopping pretty-mush-there cause the was...) - either to expensive, to red neck, altitude to high (I've got a silly heart that gives me fits walking up steps).

We took long and thought seriously at Central and South America. There again we ran into shaky governments and restrictions on what I could grow and treat my cancer. Other than my abnormal heart and cancer, I'm quite healthy. So we've turned to Portugal.