Welcome to the forum! Again, answers to some questions would help us. Have you traveled in Europe before? what is you method of transportation?
You are dedicating one day to Tuscany. For reference sake, Tuscany is the size of New Hampshire. Do you feel you could adequately see New Hampshire in one day? We spent 10 days in Tuscany a few years back and barely scratched the surface.
Your travel times are unrealistic. You are forgetting all that is involved in moving from one location to a another. Packing, checking out, getting to the train station early, actually traveling, then getting to your hotel and checking in can make your 2 hour travel time be actually more than 1/2 a day.
In an attempt to see everything, you'll end up seeing nothing. Take everything south of Rome off your itinerary for this trip. Alternately, take everything north of Rome off. Then take what's left and whittle it down even more.
Finally for a 2 week trip I'd build in at least 2 "down" days with nothing on your schedule. That will allow you a chance to be flexible. You'll discover something you want to do and will have time. For instance, when we spent a week in Loches, France, we found out about a tiny village name Chedigny, which is famous for the roses throughout the town. Since we had built in a down day, it was easy for us to use it to visit Chedigny and the gorgeous countryside nearby.