Well, this was my first overseas trip in my entire life. I went to Italy (FINALLY) and in a nutshell did a tour (mostly in the north) and here's a map of every city I went to.
Here's a rating of every city
Milan: 8/10
Florence: 10/10
Siena: 10/10
San Gimignano: 8/10
Pesaro: 9/10
Sorrento: 8/10
Positano: 10/10
Amalfi: 9/10
Salerno: 8/10
Italy as a whole: 10/10 Loved it