The time of day has huge influence around here (lat 30-35 south) in how the shade is useful or not.
Also, I would like to propose the opposite use case, a non-shade-optimized (or sun-optimized) route, as is what you look for, e.g., in winter, specially in early morning, to walk along the sidewalks where the sun shines, as it is much more warm and comfortable than walk along the shadowed ones.