I think trying to do Tuscany and CT in four days would defeat your intent of avoiding jumping around from city to city, hotel to hotel.
The hardest part of visiting Italy or any European country is to come to terms with the knowledge you can't do and see everything you want. Planning too much is inevitable since Italy has so much to offer. You can run yourself ragged and still not see everything on your list. When we went to Tuscany recently, we ended up dropping Montepulciano, Lucca and Assisi from our original plans.
For us the magic happened in the smaller moments - spending an hour or so with an artist in his gallery and frame shop in Greve, shopping at the local grocery store or spending an extravagant amount of time at a food and wine pairing. If you are rushing from one must see site to another, you'll miss that magic. I can't live my life in fear of never being able to go back - it would have wrecked the wonderful time we did have. I've got four more trips to Italy mapped out in my head. I'm sure we'll make one and I hope we make them all.