Portugal or Spain to retire
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We did 2 weeks in Portugal a couple years ago, it wasn't enough time to see more than the major cities/areas. But that was partially because we wanted to see all the stuff. We just completed a week in Barcelona. I feel like we had a good sense of what the city has to offer and we got to site see. Originally, I was wanting to spend 2 weeks touring around Spain, but I realized we would only get a couple days in each major city. Hope that helps.
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Two years ago we took a month to visit Madrid and major cities in northern Spain: Santiago de Compostela, Gijón, Oviedo, Bilbao, and also Zaragoza because it was somewhat on the way back to Madrid. We had already decided on which climate we'd want to live in, which meant we didn't waste time in areas we weren't interested in inhabiting. It was a great trip and have us a good idea of where we'd be comfortable. We loved Oviedo so much we looked up a couple expats there and had a lovely lunch with them. It really helps to talk face to face with people who live there.