My family is traveling in Italy and in addition to some time spent in Florence and Rome we have set aside 7-8 days to spend in the Cinque Terre and Tuscany/Umbria. Our current plan is to take the train to Vernazza and stay three nights in the Cinque Terre then take the train back to Florence and rent a car to see Tuscany/Umbria. Assisi is a must-see for us and we'd like to spend at least one night there but we also are drawn to the Chianti region, Siena and Montepulciano. We like to walk and cycle but we also want to experience live in some of the towns. We were thinking for taking a slow drive through Chianti (Radda, Castellina, Siena (spend some time there) and onto Montepulciano where we would stay for one night (is that to much to do in one day and is the it best way to spend our day?) Should we just head straight to Siena on the larger highway and then also see the Val d'Orsay before we overnight in Montepulciano. We were thinking that the next day we would head directly to Assisi and see the sights, followed by an additional day of cycling near Assisi (any suggestions on where to rent, get a guide, etc.) Any suggestions are greatly appreciated!