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Where to stay in Tuscany

We are traveling to Italy in October and are debating about how to spend our time in Tuscany. We have six days planned, and had thought we'd stay the first 2 nights in Florence, then move to a villa in a nearby hill town with a car so we can explore the area. The first few hotels we have checked in to are booked, so it's making us consider just doing the villa for all six nights and taking day trips into Florence. Any input about that? And, do you have suggestions for where to stay in Tuscany? We'll be coming from Venice, and heading to Florence when we leave. Thanks!