I took this tour in October, 2016, wonderful memories. I'm still friends with several of my tourmates, I went as a solo. In trying to recall what I did in my free time, I mostly went around with others to explore neighborhoods, etc. One afternoon in Rome, we walked all over trying to find a restaurant that served artichokes because they were in season. We did not find that restaurant but we found another one and had a fun lunch! No artichokes though.
You will not run out of things to do.
Lake Como, we went on the boat ride and toured the Villa Carlotta and its extensive gardens. Cinque Terre, we took the boat all the way to the last village and then went to each of the 5 villages via train, a most fun day! We hiked in the Dolomites, woke up that morning with snow on the ground, more of a dusting.
Umbria, we stayed at a Winery and Resort, can't remember the name now. On a free day, a bunch of us went to Orvieto and explored, a magnificent cathedral and toured a small Museum devoted to Etruscan culture.
In Florence, we went to the Pitti Palace, amazing place with art you cannot believe. Also, some of our tourmates climbed the 400, approx., steps to the top of the Duomo.
I hope you will write a trip report when you come back!