We loved the VF because it felt to us what we imagine the
Camino Frances might have felt like 25 years ago. Indeed of the pilgrimage routes we have walked, this was one of our favorites. There was plenty of accommodation (lots of good religious institutions) and everybody along the way was very friendly and helpful - the Italians are not yet jaded with pilgrims. Almost every night we stayed with at least one or two pilgrims so there was enough camaraderie. Many pilgrims seem to plan their trip around arriving in Rome for a day when the Pope will be in St. Peter's Square so it would be useful to work your plans backwards from this. The Italians are really working on getting the VF off big roads but there is still some unpleasant walking and a couple of places where a bus would be a safer option, and sometimes one has to walk a very large loop to avoid the roads. Generally, however, the walking is pretty straight forward and the balisage is pretty good. The terrain is wonderfully varied, from the Po Valley, to the coast, to the mountains, to the hills of Tuscany.
I was going to add a list of some places that were really excellent to stay but realize it's a very long list. I'd be happy to send you our list if you are interested and also to answer any other questions. Unlike on the camino, few of the places have kitchens but pasta and pizza are ubiquitous so eating does not have to be expensive.