Hi, and welcome to the Forum
The route from Lisbon to Evora, Beja, Serpa, and the Spanish border is interesting. Evora is an especially nice place. That route travels through mostly rural areas and small towns. However, transportation from your terminus might be a challenge. Southern Portugal is very warm during the summer, with temperatures over 40C.
We rode this route on our way to Valencia, Spain, and it may not be my first choice if I was just going to tour Portugal. Maybe some of the folks that have ridden in the northern part of the country might have some ideas. We really liked Portugal and would go back there if we had the chance.
Adventure Cycling Magazine had two articles on riding in Portugal. They were in two separate issues which just came out in the last 3 months. If you can find copies they are good references, and perked my interest in seeing more of a wonderful country.
Yes, that means do not enter