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Trip planning--Portugal and Spain

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We’re beginning to organize a 2016 Spring trip to Portugal and northern Spain and need plenty of advice.

In Portugal we’re interested in Porto and the Douro river region. In northern Spain we’d like to spend time in Leon, Burgos, Santiago de Compostela, Santillana del Mar for Altamira cave paintings, Bilbao for Art museum, and San Sebastian. We’d like to concentrate on medieval buildings, art, and wine. We also plan to schedule wine day trips to the wine regions of Ribera del Duero and Rioja from Leon and Burgos.

How do we go about stringing these cities together? Weather wise, should the cities in Spain be placed before or after the Portugal portion? We’ll most likely travel in April and the first part of May, and would like the trip to be about three weeks long. We’re flexible with time.

We plan on using public transportation, trains and buses. In Portugal we’re considering a week long river cruise with a day trip add-on to Salamanca by one of several known cruise companies, or a tour by coach with a local agency in Portugal - inDouro. Does anyone have any suggestions on how to do the Douro river region? Anyone use a local tour agency there?

We’ll either fly into or out of Porto. Would Madrid be the other flight city? We’ve been to Madrid, Barcelona, and some other, more southern parts of Spain before (as well as Lisbon, Portugal), so we’d like different arrival and departure cities if it’s logical.

Does anyone have suggestions on any or all parts of this trip?

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