Hello! My partner and I are driving this week from Milan to Siena, and are trying now to decide our route, and where we might stop to eat and sleep! We have four days for the drive, and we're open to lots of possibilities -- we're happy to adventure or detour. We are less interested in eating upscale (though not opposed to it) -- looking for: special, small spots? Very traditional and delicious -- or unexpected and interesting? We are definitely more interested in places that fit under the cheesy travel-guide phrase "off the beaten path," or at least, not filled with only tourists. But really, we just like to have lovely experiences, meet friendly people, taste new things, etc.
At this point we are just looking at a map and choosing roads and towns at random, so all advice is welcome! Any gems we should put on our map?