The Chianti region in Tuscany is riding heaven. The InGamba cycling tour operates out of there, and check out their routes on Strava, and you will have a great time. The road are winding but beautiful, drivers are super aware of cyclists, and you have a little towns dotted all around, everyone 10-20 miles, where you can stop for breaks. Gaiole in Chianti is where the Eroica rides start, from there, you can get to the Strada Bianca which to me is simply the best cycling experience one can ever have.