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It's actually pretty interesting to see how although the geography of an area will pretty much dictate that there *shall* be a major city here, in most cases those "natural sites" are more of a broadly defined region. The settlement of those regions tends to have multiple separate settlements...

Another example from firsthand experience: the Charles River forms the border between the cities of Boston and Cambridge. In fact, Cambridge -- originally "Newe Town" -- was settled specifically as a more defensible site than Boston, because the sheer size of the natural harbor made it...

Planned cities are historically very much the exception rather than the rule. They usually existed when a ruler decided to make a glorious new capital city, where planning was possible because *no one lived there* until the new city was built.

As for "cities that sprawl across rivers" -- Portland is an example of such, as it exists on both sides of the Willamette River. On the other hand, the original settlement of Portland was strictly on the west side of the river, with the settlement on the east side of the river originally being...

Just to step in on this point -- head of navigation is super important in early cities. The confluence of the Columbia and Willamette rivers is pretty much an inherent place for a port city, but the *exact* location of the city is very much a matter of navigation. And historically, there were...