Logical order of itinerary

With 16-17 nights, I wouldn’t go to Madeira. It will not be slowing down but will add the stress and most of two days to get there and back. And, if there are cruise ships in port, it will potentially as crowded as the mainland.

If you haven’t purchased your flights, fly into Lisbon and out of Porto or vise versa.

If you want some quieter spots for that four nights, consider Coimbra and/or Évora for a couple of nights. Both will have tourists but not as many as the two main cities. Evora is easy from Lisbon - and Coimbra is easy on the way between Lisbon and Porto.

Staying in the Douro will be a bit quieter. If you are coming early in September, you might want to start in the Douro. You might be able to be there during ‘crush’ time, which is great.

You could also add some days to Porto and side trip to Braga. I just returned from my first trip there and really enjoyed it. It’s easy on the bus or train and has plenty for 2-3 nights.

Thank you Kathryn. I am beginning to agree with you that I don't have enough days to spend 2 of them flying and hanging around airports. I am planning on staying at least one night in Douro Valley and maybe a couple of nights in a lovely Posada in Vianna Do Costello that can be easily reached by train from Porto. Thanks again for your suggestions.

As part of my recent trip to Braga, we visited Viana de Costello - at least the large church on the mountain overlooking the town. Sorry, I can’t remember the name of it. But, it has a posada, which looked lovely from the outside. If that is the one you are thinking of, be aware it’s very far up the mountain with nothing else than the church around it. If you’re looking for peace and quiet and killer views, it would be great.

Thanks for the update Kathryn, I think that is exactly what I will be looking for at the end of 14 days touring!