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Portugal/Spain

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Just in the consideration phase for a 3 wk trip to either Portugal and/or Spain. Don't know much about the region and am just now starting to research. Was wondering when the better time of year for travel would be (not to cold and not much rain) and has anyone ever been on a riverboat cruise in these areas? If so, company name and experience would be much appreciated. Is self-driving problematic?? We've been to most of Asia and wouldn't want to get behind a wheel myself there (difficult enough as a passenger) and was wondering if this area would be as difficult to self-navigate. We've driven all over NZ and the land down under with no problems but much less populated than other areas. Any information (weather, must see locations and any other relevant info) would be greatly appreciated.

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