When I studied abroad in Italy in college, I was able to visit Siena on a day trip and I absolutely loved it! I remember having the most amazing lunch of wine and pizza on the Piazza del Campo, followed, for some unknown reason, by a lively serenade from a two-man Italian band. All in all, I found this small city so entertaining that when planning this trip, I knew I wanted to spend more time there.
We stayed at Siena's Grand Hotel Continental, a boutique five star hotel originally built as an aristocratic palace in the 17th century. The hotel was perfect in every single way: unbeatable, location, friendly staff, good room size, clean, free (and delicious) breakfast and incredible views!
That night, we enjoyed a light dinner at a cafe situated right on the aforementioned Piazza del Campo, which is Siena's medieval town square. The "square" itself is actually a shell-shaped public space made of red brick and travertine - it is one of my favorite spots in Italy.