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What size would a city have to be (in terms of square miles/ km of urbanized area) to be big enough to be able to get lost in, but no so big that it's huge?
What about population, population density and street density (how small the blocks are)?
What are some good examples of cities that fit your criteria?
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I think it's more important that a city has a defined edge than a specific size/density.
For example looking at the bay area, San Francisco has a size of 46 square miles and a population of 837k. Where as another city like "Berkeley" only has 17 square miles and only 117k people. The problem with Berkeley is that it blends into many cities around it. So you don't know when you leave one city and enter another. With San Francisco it's uniquely surrounded by water on three sides. I've gotten more lost in Berkeley than San Francisco.