Donna, thank you for your suggestions. We are focusing on Greve in Chianti for 3 days and Buonoconvento in the Val d'orcia for 4 days. In each case we will stay at an Agriturismo and gain exposure to winemaking, olive oil production, honey production, and saffron harvesting. We would take day trips to Florence, San Gimignano, Volterra, and tour the Chianti countryside from Greve. On the drive to Val d'orcia we will see Sienna. From Buonoconvento we would see Montalcino, Montepulciano, and Cortona. On our drive to Rome for our departure flight we will visit Orvietto.
In addition to touring the historic sites and enjoying the Tuscan food, we plan to taste the wines from each of the regions: Chianti and Super Tuscans in the Chianti region, Vernaccia in San Gimignano, Brunellos and Rossos in Montalcino, Vino Nobile di Montepulciano in Montepulciano, and Orviettos in Orvietto.
Does this itinerary make sense? Are we overlooking an area of particular interest? We will be arriving in the first week of May, 2016. I believe tourist crowds should be lesser then one month later.