Not grandparent but I was rather thinking of medieval city centers in Italy or Spain.

edit: Case in point:

https://maps.app.goo.gl/xxYQWHrzSMES8HPL8

This is an alley in Coimbra, Portugal. A couple years ago I stayed at a hotel in this very street and took a cab from the train station. The driver could have stopped in the praça below and told me to walk 15m up. Instead the guy went all the way up then curved through 5-10 alleys like that to drop me off right right in front of my place. At a significant speed as well. It was one of the craziest car rides I've ever experienced.