My very generous friend with a car offered to take me wherever I wanted to go in Italy in the limited time I have left in order to help me finish my Italy bucket list. While there are TONS of beautiful towns and whole regions I haven't visited, I really wanted to see a bit more of Tuscany since it's so close and densely packed with picturesque hill towns. We ended up making a day of it - drving to Montepulciano for lunch, shopping, wine tasting and just generally touristing.
The day was lovely and we seemed to have magical timing - got a great parking spot, the perfect lunch table overlooking the valley, and missing out on the big tourist crowds. I'd certainly recommend a visit if you have a car. Otherwise it's a bit challenging to reach.
Finally, two local crafsmen I thought deserved a shoutout. Both were kind enough to let us watch them work and explained a bit about the artistic processes they use - in case the pictures aren't super clear one makes wood collages, the other makes mosaics. A piece from either artist would be a great souvenir but I passed up the chance so I could spend all that hard earned money on gelato - priorities!