I have the good fortune to be spending nearly 90 days in Italy this winter and will be spending the last two weeks of February in Tuscany. I will be arriving in Florence after spending six nights in Venice. Prior to that I will have been south to Rome, Naples, and down to Sicily. I will also have spent time in Orvieto, Assisi, and Ravenna before Venice.
My initial plan was six nights in Florence, three in Lucca, and seven in Siena. The Florence time would be mostly in the city but also perhaps some of the neighboring towns as day trips. From Lucca, I would do a day trip to Pisa.
I had considered staying in a couple of different places around Siena, but lately thinking of basing in one town and doing day trips to a number of the surrounding towns such as Volterra, San Gimignano, Montepulciano, Pienza, and Montalcino. My question is does it make sense to base in Siena for a week to see that city plus all of these other smaller towns? Or should I break it up and stay in a couple of different places in that area. It will be the 2nd half of February so a bit cold and wet. I am from Seattle so I don't mind that so much as long as the roads are passable without chains. My interests include architecture, art, and history so all of these places are of interest. Of course good food and wine are always on the list. Any advice for about 16 nights in Tuscany in February would be appreciated.