Itinerary opinions please

I saw in you separate post that you'll have a car. I first visited Obidos almost 40years ago, on a recommendation that it was a really cool small town, on a first rip to Portugal. While it was a memorable visit, I figured I'd never be there again. Then on a trip to Spain in 2002 with a weeklong side trip to Lisbon and points north, we wound up sending a night there again, as much because it was getting toward evening and we needed a place to sleep, and not so much because it was a must-see destination. But since every trip to Portugal has wound up with a stay in Obidos, maybe I'd have to say that a trip to the country is incomplete without including Obidos in the intinerary!

Evora, however, IS a must-see. The old part of the city is a fascinating collection of beautiful and historic structures, and although we never stayed in a Pousada, we had dinner one of our nights at the one in Evora - a worthwhile splurge. Just outside of town (handy to reach with a rental car) is a prehistoric dolmen - the first one we'd ever come across, before subsequent trips to Ireland and Brittany - and it struck a real chord to seek them out on subsequent trips. That was a totally unexpected, but completely worthwhile experience.

We didn't get far enough north to make it to Porto that 2002 trip, as we had to get back to Spain for our return flight, but heading east through the cork tree groves was another memorable experience - I kept looking for Ferdinand the Bull (a favorite book as a kid) under one of the trees, smelling the flowers.

Sounds like you have time after the wedding as well? Total number of days available will influence recommendations on how many places you can visit. We did a three week loop of the country, mainly one night stays, visiting many of the places you mention.