Italian Hill Towns are some of the most magical places on Earth
Why do we have such an innate attraction to these places?

There seem to be a few reasons, from their wonderful architecture, organic & highly walkable streets, an intimate human scale, warm natural materials, and the humbling power of connecting to centuries old culture.
But I'm going to offer another, less explored reason here.

Nearly all Italian Hill Towns are discrete, self-contained places. This means there's no sprawl leading up to them. One goes from a beautiful countryside or natural area, directly into the heart of a magical village.
Why is it important that the countryside gives way directly to the village?

Because the experience becomes complete, fully immersive, & untainted by less lovely places. You go from beauty to beauty, none of the messy in between. You can see this on aerials of these towns.
This is in stark contrast to a place like Disney. Yes, the experience may be great once you're within the the parks borders, but the journey to to the Magic Kingdom is anything but, driving through miles of strip malls & subdivisions, acres of parking.

While this is easier to accomplish for smaller towns like Civita di Bagnoregio (11-20 inhabitants), or San Gimignano (~7,500), remarkably, the condition of self-contained places can extend up to cities the size of Siena (greater than 50,000)
When we cut out the middle between countryside & village, we create places that are more walkable, sustainable, and in my opinion, more lovely.

It's the best of all worlds: we conserve more of the natural environment, we interact with our community more, and it's more beautiful!
And of course, as Andrew mentions, the views!

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Nice thread. Same thing in Greece of course.