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Hub Agriturismos for 15-17 dayTuscany/Umbria tour & wine drive - couple in 60s

Couple in 60s planning one last Italy trip to Tuscany/Umbria to experience countryside, hill towns & wineries, driving on our own. Considering September or next May. Can fly into Milan or Venice & want to rent a car. We'd like to visit the following towns (perhaps too many) help us select the "must see" stops and suggest Agriturismos and particular wineries. We want to experience good wine, cheese, local markets, truffle hunt. Looking for maybe three hubs for 3-4 nights each- thinking of Chianti villages; Montepulciano & Montalcino; Orvietta, Assissi, Gubbio & San Marina. Welcome your thoughts on which towns can we visit each day.
From our hubs we'd like to visit:
Luca & Pisa
San Gimignano
Volterra
Chianti Region along the Chiantigiana route
Cortona
Montepulciano
Montalcino
Assissi
Orvietto & Civita di Bagnoregio
Gubbio
San Marina
Ravenna & Montone

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We saw that sight before we posted and that gave us confidence that the hub base idea works. What we don't know is how many hubs we need and where. For example, do we explore Chianti country from one hub and is it Greves or outside Sienna; and do we need another hub to see Luca, Pisa, San Gimignano & Volterra and if so what works best? To see Cortona, Montalcino, Multipiciano, Gubbia is this one or more home base? Can Assissi & Orvietta be seen from one base and if so where to stay? We don't want to be doing a lot of driving each day, (at this age, 2 or more hours each way would be too much for us in one day) particularly if we go wine tasting, so we know we have to get our base locations right. We're trying to make this more relaxing "dolca vita", rather than if it's Tuesday this must be Belgium-like. So we really appreciate your specific suggestions based on experience.