The trick to taking day trips in Tuscany is to stay flexible and if at all possible, make your plans day by day instead of sticking to a tight schedule.
During our week in Tuscany, we took several day trips to big towns as well as off the beaten path destinations.. We knew that the Palio would be in Siena, and as much as it is a sight to see, we also knew that we did not want to contend with the crowds. So we went to Siena on the day before the Palio, so that the city would be decorated in preparation, but now overly crowded with festival goers.
We walked. We shopped (Just a wee bit. Thank you Geox and Furla for being so accommodating and having such a great selection). We ate.
We did not go into one single museum. Not one. In part because we are trying to very deliberate in making sure that we pick and choose things that will be engaging for Principessa. But also because when you spend only one day in a place, we are fans of walking and exploring.
Of course, no day trip (especially during a hot summer day) is finished until you have had gelato.
Or,at the very least, getting gelato all over your face and hands.