”I am thinking 2 days per stop.”
I switch locations more than most on this forum, and I stay two nights at a lot of locations. But, I am very stingy with my travel time between locations. It’s typically 1-2 hours by train max, and I am at the next location. Being very efficient with my packing and hotel location, I’m at the next city with my bag left off around 10:30am and out enjoying the new city. That is not at all what you will experience.
Athens to Santorini is 5 hours.
Portugal to Milan is about 9 hours door-to-door.
Etc.
Essentially this is a plan where you will waste one day of travel between each location, so any 2-night stop is an evening/night and one day. Realistically, this is a “5-days of vacation” trip.
So, to be helpful for your specific itinerary, what are you wanting to see & do? The interests you list could generically be fulfilled in most places in Europe. From your list, how about a Spain/France trip? Maybe Barcelona, plus the Nice, France & Lourdes area.
Or a Greece trip?
If you only care about Milan, I would skip Italy.