Siena is another one of the underrated places in Italy. It should definitely be considered when planning your Italy itinerary. It makes for a great day trip from Florence for example if you’re short on time, so very little excuse not to seek it out. This Tuscan hill town is worthy and is for sure one of the best medieval cities in the Tuscan region. Here are 12 reasons to visit Siena, especially in the fall. It has a lot in common with Perugia, another lovely city we liked a whole lot.