Basecamps in Provence and Tuscany/Umbria

Tuscany: anywhere along the freeway corridor between Florence and Siena. The Alta Val D'Elsa is the most central (roughly between Certaldo and Monteriggioni).
Umbria: in or near Assisi is the most central to most Umbrian destinations. Orvieto, to the south of Umbria is also popular.

Note that the areas mentioned are bigger than they look on a world map. Tuscany alone is bigger than the entire state of Massachusetts and many towns are accessible only through slow curvy mountain highways where you can hardly drive faster than 25-30mph (40-50km/h)

We rented a farm house about 5km outside of Cortona, which is in Tuscany, but borders Umbria. We wanted to be have a long list of options of things to do without spending hours and hours driving.

So here's how our week looked:

Day 1- arrived about dusk

Day 2- Explored Cortona for the day

Day 3- Train to Florence for a soccer match/dinner in Cortona

Day 4- Cooking class in Cortona- 10 am- 8pm- cooking socializing, drinking wine, etc.

Day 5- Drove to Siena for the day/dinner in Cortona

Day 6- Early train to Florence for the day for sightseeing (Segue tour). 8pm train back

Day 7- Montalcino-explored and tasted wine and had great lunch/late afternoon and dinner at farmhouse

Day 8- Drove through Cianti region- stopped at a winery for tour and great lunch on way to Florence airport for 6 pm flight

Other options that were on the list were Assisi, Rome for a day, Orvieta, and other hill towns whose names I can't recall.

Day 1 Pick up rental car in Florence, then to a base somewhere in Chianti, or near Monteriggioni
Day 2 Excursion to Arezzo, Cortona
Day 3 Day in Siena
Day 4 Excursion to Montepulciano, Pienza, Montalcino
Day 5 Excursion to San Gimignano, Volterra
Day 6 Drive from Chianti to Pisa via Lucca and drop off rental car