I've posted elsewhere about our stay at Castiglion del Bosco in Montalcino. We used our travel day after leaving there to visit a few towns in Tuscany before driving on to Florence.
We hired a driver - for us it was much more enjoyable not having to figure out how and where to park in Siena, especially. We also hired a guide in Siena, which, I think, if you are only going to be there for a few hours, is a must. I would love to have spent a few days in Siena, of course - maybe next time.
One comment regarding accessibility: Siena is NOT friendly to anyone who cannot climb up and down inclines. I am pretty sure our guide was part mountain goat and I greatly admired her strength and speed, but I am afflicted with back problems and so there was a considerable cost associated with trekking down and back up again from the Piazza del Campo. Yes, of course, it had to be done, but it is a town (and, for that matter, a country) for the able-bodied.
From Siena, we went on to Monterrigioni, which was one of my favorite stops of the trip. Very small and not yet totally spoiled but probably will be soon because it is so charming. I saw some of the better retail offerings of our trip there.
Up the hill from Monterrigio is San Gimignano, which is an extremely popular destination. A little too popular for my tastes. The lines of tourists (yes, I know that I am one, but that doesn't stop me from despising the rest of them) jostling for entrance to the "best" gelaterias and crowding the shops to buy "Italian" (but probably made in China) leather was a bit wearying.
I have posted photos from all three places here:
https://polloplayer.wordpress.com/20...ip-in-tuscany/