Hi Rowdy, you will love Porto! Make sure you spend a day there before you start walking, the city is amazing!
I usually book private rooms for my first and last days (to recover from the long flight and to rest from the walk), but it depends on what you like and I am sure that here in the forum people will have great suggestions.
I really enjoyed Hotel Moov Centro, in the Old city - price of an Ibis hotel, but with lovely service. I also heard lovely things about the Poets Inn, near the Torre dos Clerigos, in the very middle of the old city.
For Santiago, there are so many options. Last time I stayed in Hotel San Clemente and was treated like a queen