There was only really one day that we spent in Siena, and while this short stay is completely do-able, I’d recommend at least two if you have the time in your itinerary. Sure, it is touristy as most of the other on the Italy ‘route’ towns and cities are, but there is a reason why it has become such a visited town.
I absolutely adored Siena, I adored its little hilly streets and its coziness, I also adored its hills and views to the incredible Tuscan countryside. We didn’t drive so most of Tuscany’s green rolling hills were appreciated from vantage points within the couple of towns we visited. All I can say is that as touristy as Siena is, with its famous shell-shaped Piazza De Campo and twisting winding alleys and orange clad rooftops, Siena still managed to steal my heart. As the sun goes down, and the hordes of tourists leave, you can get sliver of the real feel of Siena.
All of my photos in Siena were taken on the day of arrival (we had bused in that morning from Rome). The second day in Siena, we did a day trip to the Tuscan town of St. Gimignano. When we returned back to Siena that evening, I just wanted to eat gelato, wander around without the camera and soak in the beautiful town without a lens in the way. It’s good for the soul of keen photographers, if only for an evening. Oh, and an early night was much needed as well.