I've spent a lot of time in Portugal. The Douro Valley is probably the most beautiful place I've been in Europe, don't just do a day trip, spend a night or two. You'll be there at harvest time, I don't know if that will be better or worse for tourists.
Porto and Lisbon are both amazing cities. Don't do too many day trips out, enjoy the cities, but certainly from Lisbon check out Sintra and Cascais.
Midway between them you can check out Peniche if you're a surfer and in Nazare the swells should be picking up if you want to watch insane people take on the biggest waves in the world.
Personally, I am not big on the Algarve (Faro and Lagos). It's Brits and Germans with their holiday rentals and while there are some beautiful cliffs it is just too touristy.
I'd rather spend my time exploring some of the other amazing wine regions like Alentejo or Dao. That will connect you more to the culture and no doubt you'll find some off the beaten track gems rather than some dudes persistently trying to sell you oversized novelty sunglasses on the beach.
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