Itinerary help - Porto or Amalfi

Addendum: we haven’t been to Assisi or Orvieto. Maybe we should just pick a town that size, with good train connections, and relax there for five nights, Thoughts on this or some place similar?

I'm a newbie traveler and haven't been to Amalfi Coast, but have been to Italy once as an adult (Venice, Florence, Rome) and Portugal 2X.

The first time I experienced Portugal (Lisbon) was part of a stopover on the way to Italy to get over jet lag. It was the favorite part of my "Italy" trip. Summer last year, I convinced my husband, who hasn't been to Europe and does not see the point in traveling, to go to Portugal with me. We focused on the northern part. He loved it. He still has no interest in traveling to Europe, but will make an exception for Portugal.

Porto is not spotless, but in transition with some building being restored and others still crumbling. It's a country where family is important and the people very warm. It's a very safe place to travel, excluding pickpockets which seem to be common everywhere. One of our activities was to wander around, including narrow walkways discovering street art (which is amazing). It's a photographer's dream. The tile work is gorgeous and the place is full of history.

As you can probably tell, I love Portugal, specifically Porto. If I could, I would buy a place and live there.

It seems best to minimize the number of countries you visit in a single trip, due to changing Covid border restrictions (although this seems to be getting better). Therefore, it feels more prudent to head to Italy!
And if you worry that the Amalfi Coast looks like Cinque Terre, there are similarities, but it still has a different flavor. Have you been to Naples, by the way?
Ischia would also be a great place to relax for 5 nights.

I like both Assisi and Orvieto; I'd favor Orvieto over Assisi for a stay as long as you are contemplating, but if I were religious, it might be different. However, before choosing one of those primarily as a base for day trips by train, you should develop a list of places you'd like to go and check the travel times on trenitalia.com. I don't think of either of those towns as being great central points for train trips. Adding buses into the mix would help--though you have to be really, really careful about bus frequencies on weekends, especially on Sundays--but really it comes down to what other places you want to see. There are places that look close on the map but involve very convoluted trips by public transportation.

Or are you thinking about renting a car? That would certainly simplify matters.

Thanks for the input. We have decided to give Porto a try. Looking forward to exploring a new country!