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Portugal & W. Spain in October

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My husband and I are spending 3 weeks in Portugal and Spain in October 2015. We fly in and out of Lisbon and have rented a car. We prefer to stay in towns and small cities for 3 or 4 nights and do day trips from there before moving on. Our loosely planned route, in no particular direction is -
Evora - visiting Cromeleque dos Almendres, Elvas, Monsaraz
Merida - or is highway thru Beja into Spain more picturesque?
Ronda and the White Towns
north thru Toledo, west to Salamanca,
into Portugal towards Gaurda
and back to Lisbon via the coast
We will spend our first 2 and last 2 nights in Lisbon and plan to visit Sintra and Cascais
Now, what I am hoping to get from you experts are suggestions of towns to use as bases and what to go see while based there. We are hoping to visit cork plantations, wineries; travel on some scenic roads; experience great sea food, wine and traditional dishes; take in flamenco dancing and markets. We like quant, upscale hotels with character in town centers so we are able to wander off to pubs or restaurants.
I have been reading this Forum for months and have a plethora of notes but cannot get it together enough to make concrete decisions and plans. All suggestions, tips, advice will help me immensely.

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