Last time we visited Tuscany we stayed in San G. and absolutely loved it. Walking thru the medieval town after the crowds went home, the restaurants with views over the beautiful countryside and the shops with pottery and anything else that a person would want to bring home from their trip. This summer we are going back to Tuscany and my husband wants to do something different - but I still want the "look and feel" of San G. Is Montepulciano the right spot for us or is there a different hilltop town that you would recommend?
We're also debating between late May (when we visited last time and loved seeing the red poppys in the fields) or early September (for something different). Any thoughts on this are appreciated as well.