Having visited Lisbon, and central and north Portugal, if I had it to do over again, I’d devote more time to the Alentejo, with its high concentration of amazing sites and experiences in a relatively small area. There’s a lifetime of exploring there, but soak it in for at least a few days. Extraordinary Evora and nearby environs are the places to start. I prefer to travel independently, but in the case of Evora—so dense in history, symbolism, and multiple cultures-- we would have missed so much without a guide. It was well worth the reasonable expense.
Rick’s recommendation of Prof. Libanio Murteira Reis was on the mark and gave us an authentic and depthful experience of this captivating area. Notwithstanding that Prof. Reis’ family extends back generations in Evora, what decidedly sets him apart is his expertise as a scholar and professor of history in the university there for thirty years and his work in sustainable tourism. We also found that he has been consulted and interviewed by the BBC, National Geographic, Michelin, Fodor’s and numerous other programs and publications. For web searching in English, he’s a bit of a well kept secret, so I reveal it here: http://www.evora-mm.pt , e-mail firstname.lastname@example.org
One would be hard pressed to find a more engaging and knowledgeable guide with a contagious passion for his home. Our trip was made memorable by the very personalized approach that seems his ardent philosophy. In one instance, knowing that one of us had China roots, he arranged on the spur of the moment with a staff member at the Ducal Palace of Vila Vicosa for us to view a special collection of blue Chinese porcelain not usually on display to the public.
Evora was an easy 1.5-hour train ride from Lisbon, even with luggage. We found the Alentejo and Portugal weather in general to mirror that of Southern California with October/November in the 70’s and 80’s. Checking in late November, the climate still seems surprisingly temperate. The Alentejo is said to be gorgeous in the spring, but I’d also be tempted to consider the winter months when lower airfares and accommodations, and less tourists might be found.
Here’s what I wish I’d read before my trip. 1) “The Best of the Alentejo” for a compilation of all the area has to offer (found at http://www.visitalentejo.pt/en/brochures/) 2) The Portuguese – A Modern History by Barry Hatton and 3) Portugal: A Companion History by Jose Hermano Saraiva. The latter two are best-reviewed and highly readable books that will enrich your experience in Evora and Portugal in general.