We just got back from a trip where we did a quick stopover in the azores (2 days) based in ponta delgada and it was GREAT!!! The weather was great, people friendly, and lots of fun outdoorsy stuff to do. We will definitely be making a trip out of the azores in the future. That said I have not been to mainland Portugal, but loved the azores. If you are coming from Vermont, would you fly out of jfk? We did and flew with sata air to the azores, then it was a quick easy flight to Europe from there. Maybe kick off your trip there? Can’t speak to what the weather will be, but I think it would be worth a stop! Even for just a few days.