Tuscany was absolutely one of my favorite stops during our month in Italy. Partly, it was the only fall weather we saw; but it's the sort of place you can tell is beautiful whether or not the leaves are dripping in yellow and orange. We stayed in a tiny hamlet called Poggio di Loro in an Airbnb that blew our minds. Not only was it cozy and beautiful, the hosts were above-and-beyond in their hospitality.
The town below the hamlet was called Loro Cuiffena, and there we had a few coffees and meals, ran some errands. We loved the owner at Ristorante Pizzeria Dimicla, which was really a standard sort of place; but he was so friendly and introduced us to Zolfini beans, changing our little vegetarian lives. We also loved the market there for local cheeses and wines, which you can't not sample when you're in Tuscany, of course.
Because of it's size, everyone in the hamlet knew we were around just hours after our arrival (or maybe even before?!); but it made the whole experience very inviting, and we felt comfortable walking around and exploring the tiny Medieval enclosures. We took some lovely drives through the winding, wooded roads and stumbled upon some other small towns. We took a hike to the Cross of Pratomagno for the most incredible views of the whole valley.
Sometimes you visit a spot and it's amazing to see it for that time; but this felt so homey, so special, I know it's an area we will return to someday.