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Extremadura (Spain) and Alentejo (Portugal)
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The following is a driving itinerary for a visit that straddles the Extremadura area of Spain and the Alentejo area of Portugal. It is the recommendation of a couple we met from Spain. They say it is tried and true, and that they and many of their friends have followed it.

Visit to the Regions of Extremadura (Spain) and Alentejo (Portugal)

Distance between towns -- Less than 100 kilometers.

Cáceres (Spain): UNESCO Patrimony of Humanity.

Plasencia (Spain): Historic city with monuments.

Trujillo (Spain): Historic city with monuments.  (Another friend tells us that Trujillo is even a better place to stay on this itinerary than Cáceres.)

(Also consider a visit to Guadalupe, with its magnificent monastery and ceramic crafts.)

Coria (Spain): Historic city with monuments.

Mérida (Spain): Best preserved Roman city. UNESCO Patrimony of Humanity.

Évora (Portugal): UNESCO Patrimony of Humanity.

Estremoz (Portugal): Historic city. The best pousada in Portugal is there, the Pousada de Santa Isabel.

Elvas (Portugal): Walled city; only accessible by pedestians.

The same Spanish couple also recommended a visit in Portugal to the cities of Porto and Coimbra:

Porto: Second city of Portugal, European City of Culture for the year 2001. It is a beautiful and peaceful city. Enjoy the sites, the food and the shopping.

Coimbra: A smaller city, but more tranquil and very historical. The first European university it there.

Food: In Extremadura, mainly ham (of Montanchez or Hijuelo) and pork.

In Portugal, mainly cod. The Spanish couple recommends barbecued cod with olive oil.