Went to Tuscany (among other places) last fall - there are some great villas in the area surrounding the hill towns - beautiful rooms overlooking olive groves, etc. - and the hill towns are fabulous. (I stayed outside Montepulciano but there are lots of other areas too)
Don't miss Sienna
And the drive to Florence is only about an hour.
Just remember it's REALLY pricey (even for Europe) in Italy these days.