Need Help Planning 2 week Tuscany Sightseeing Trip


New member
My wife and I are planning a 2 week holiday mid September to see and experience Tuscany. From my research here are the things that interest us. I would appreciate help in choosing the more important sights (and dropping the minor ones) as well as helping plan the trip i.e. where to stay etc. I am thinking I will arrive in Florence, sight see Florence for two days by foot and then rent a car to travel around Tuscany. I am hoping I could pick a couple of places to stay so we are not packing/unpacking each day. We are fit and love walking. Can I do the trip with picking 2 or 3 places to stay with day trips around the location? If so which places should I pick?
A big THANK YOU in appreciation! Grazie!!
1. Etruscan villages: Sovana, Pitigliano, Viterbo, Tarquinia
2. Monasteries: Assisi, Perugia, Cortona, Santuario Della Verna, Poppi, Monastero & Sacro Eremo Di Camaldoli, Abbazia Di Monte Oliveto Maggiore
3. Piero Della Francesca's paintings: Urbino, Passo Di Bocca Trabaria, Sanse Polcro, Monterchi, Arezzo
4. Wine Tour: Castello Di Varrazano, Greve in Chianti, Badia a Pasignano, Panzano, Castello di Ama, Montalcino, Montepulciano
5. Tuscan Landscapes: Siena, Pisa, San Quirico, Pienza, Osteria La Porta, Chiusi, Orvieto