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The question assumes medieval cities were not pleasant places to live, and I believe this was not necessarily the case.

There is an old German saying, from the Middle Ages, "Stadtluft macht frei." It means city air makes one free. It refers to economic and political conditions, but it reflects a sentiment of the time.

It is hard to imagine Florence being unpleasant unless there was something very unusual going on.

Cities did have problems. Overcrowding of slums was a problem. Sanitary conditions in the Middle Ages were fairly uniformly bad because people did not understand how diseases spread. It was hard to find work in bad times. And cities doubtless had higher crime rates than towns or villages.

On the other hand, there were real efforts to deal with these problems, and some of them were effective. London, for example, began building its water infrastructure in 1247, with a conduit that brought spring water into the city. Similar work was done elsewhere earlier.

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Q: Why medieval cities were not pleasnt places to live?
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