Question for any Italian Blenders!

Hi Blenders! If any of you are from Italy, or have traveled through Italy, I have a couple of questions! There is the possibility that I may be going to Italy within the next couple of years with my mom (I like to plan ahead!).

1) what is the best time of year to go so that the weather is comfortable and not too hot?

2) I traveled to Italy over 20 years ago with my mom and visited Rome, Milan, Florence and Como. This time around we are considering smaller towns. What are some wonderful smaller towns that would be worth seeing or staying in? Any region of Italy would do!

Thanks in advance!