I'm planning a (first) trip to Italy in a few weeks and I'm allotting 4 days in between Rome and Florence for Tuscany. I was thinking of spending 3 nights in a small town (Montefollonico) near Pienza and the last night in Siena. Food-wise, would it be better to sleep in some Tuscan towns than others? Or is everything close enough together that it doesn't matter? Are there any particular eating experiences in Tuscany that I shouldn't miss?
I'm also spending one night in Bologna between Florence and Venice. I felt like I shouldn't miss the opportunity for a meal or two in Italy's "food capital". How would you spend your one dinner (and possibly lunch, too) in Bologna?