July 2009 and July 2015
I've traveled to Italy on two specific occasions. The first was back in 2009 as part of a family trip with my Aunt and Uncle. We had a brief stopover in Rome for a couple of days before heading to our primary destination: Sicily. The reason being, my grandfather on that side of the family (my Mom's side) is Sicilian and still has family back in the old country. We went to go see them, which, for me, was the first time I'd ever met them. So, for me, the Sicily part of the trip sticks a little more in my memory, but as you can imagine, the two places are incredibly different and distinct in their own ways.
My second trip was in the 2015 backpacking trip with Blake, just after Slovakia and before Ireland. This time we stayed for a few days in Milan, thus completing the north, middle and south trifecta for me, and naturally, since this particular trip was with a friend instead of family, it went much differently.