My wife and I are spending 2 nights each in Tuscany and Umbria in early October en route from Bologna to Rome. I have booked hotels in Siena (Palazzo Ravizza) and Perugia (Brufani Palace) to serve as our home bases from which to explore surrounding the area and towns (not to mention those cities themselves). I like the idea of having a city to come back to in the evenings for dinner and passeggiatta versus having to negotiate dark country roads to find dinner somewhere if we were staying in a remote locale in the countryside. But I'm beginning to have second thoughts after reading some of the posts about some of the small, beautiful hotels in places like Radda, Pienza and Orvieto - you seem to have the advantage of staying in charming, less touristy venues but with more than enough local dining options and evening activity. I would appreciate opinions on the subject of citta versus cittadini and any further recs on where to stay in the latter.