Medieval opinions on cities were as varied then as they are now. Some people liked them, others hated them. Some thought they promoted virtue and commonwealth, others thought they promoted sin and vice. For example, take these two opposing views of medieval London:

From William FitzStephen, a proud Londoner of the twelfth century, describing the dining options of the city:

"Every morning you can find those carrying on their various trades, those selling specific types of goods, and those who hire themselves out as labourers, each in their particular locations engaged in their tasks. Nor should I forget to mention that there is in London, on the river bank amidst the ships, the wine for sale, and the storerooms for wine, a public cookshop. On a daily basis there, depending on the season, can be found fried or boiled foods and dishes, fish large and small, meat – lower quality for the poor, finer cuts for the wealthy – game and fowl (large and small). If friends arrive unexpectedly at the home of some citizen and they, tired and hungry after their journey, prefer not to wait until food may be got in and cooked, or "till servants bring water for hands and bread", they can in the meantime pay a quick visit to the riverside, where anything they might desire is immediately available. No matter how great the number of soldiers or travellers coming in or going out of the city, at whatever hour of day or night, so that those arriving do not have to go without a meal for too long or those departing leave on empty stomachs, they can choose to detour there and take whatever refreshment each needs. Those with a fancy for delicacies can obtain for themselves the meat of goose, guinea-hen or woodcock – finding what they're after is no great chore, since all the delicacies are set out in front of them. This is an exemplar of a public cookshop that provides a service to a city and is an asset to city life. Hence, as we read in Plato's Gorgias, cookery is a flattery and imitation of medicine, the fourth of the arts of civic life."

He goes on to describe beautiful public and private gardens, the city's security, its proud history, the quality of its citizens etc. To William, London was unambiguously fantastic. He later says "The only problems that plague London are the idiots who drink to excess and the frequency of fires.", which in the grand scheme of things are pretty minor.

But here is Richard of Devizes, a monk from Winchester giving his opinion on London a few decades after William FitzStephen:

"You will come to London. Behold, I warn you, whatever manner of evil or perversity there is in any and all parts of the world, you will find in that city alone. Go not to the dances of panders, nor mix yourself up with the herds of the stews; avoid the talus and the dice, the theatre and the tavern. You will find more boasters there than in all of France, while the number of flatterers is infinite. Stage players, buffoons, those that have no hair on their bodies, Garamantes, pickthanks, catamites, effeminate sodomites, lewd musical girls, junkies, lustful persons, fortune-tellers, extortioners, night strollers, magicians, mimics, common beggars, layabouts - this whole crew has filled every house. So if you do not wish to live with the shameful, you will not dwell in London. I am not speaking against the learned; whether monks or Jews; although, from their dwelling together with such evil persons, I should esteem them less perfect there than elsewhere."

Richard goes on for page after page going through every notable town in England saying how sinful and degraded the people there are, as he strongly associates urban living with sin and vice, but he reserves a special hatred for London.

And of course, different cities were different. Ibn Jubayr, a pilgrim from southern Iberia who travelled to the Holy Land in the twelfth century, gives his opinion on most of the places he went, and they vary. In his description of Messina in Sicily, he deems the city too crowded (a common complaint of Ibn Jubayr, he's not a fan of crowds), too smelly, too dirty, too tense. The only nice thing he has to say about Messina is that it is remarkably safe, even for foreigners:

"This city is the mart of the merchant infidels, the focus of ships from the world over, and thronging always with companies of travellers by reason of the lowness of prices. But it is cheerless because of the unbelief, no Muslim being settled there. Teeming with worshippers of the Cross, it chokes its inhabitants, and constricts them almost to strangling. It is full of smells and filth; and churlish too, for the stranger will find there no courtesy. Its markets are animated and teeming, and it has ample commodities to ensure a luxurious life. Your days and nights in this town you will pass in full security, even though your countenance, your manners, and your tongue are strange."

When he reached Palermo, he had a rather different opinion:

"It is the metropolis of these islands, combining the benefits of wealth and splendour, and having all that you could wish of beauty, real or apparent, and all the needs of subsistence, mature and fresh. It is an ancient and elegant city, magnificent and gracious, and seductive to look upon. Proudly set between its open spaces and plains filled with gardens, with broad roads and avenues, it dazzles the eyes with its perfection. It is a wonderful place, build in the Cordoba style, entirely from cut stone known as kadhan. A river splits the town, and four springs gush in its suburbs. The King, to whom it is his world, has embellished it to perfection and taken it as the capital of his Frankish kingdom (may God destroy it)."

These are among the most detailed descriptions of cities we have from the Middle Ages. Although many of them are primarily concerned with things like how cramped the streets are, how the food is, prices at markets etc., there is often a moral component. To FitzStephen, there was a greatness that emerged when people came together to live in cities. His view was a very romantic one, and he even links the city to Plato's writing on the basis of its public kitchens. To FitzStephen, a well run city produces a sense of commonwealth, which in turn produces good citizens who come together in times of strife and celebrate together in times of plenty. Richard of Devizes holds the exact opposite view. He believes that cities compressed people into an environment inclined toward immorality that ultimately falls to sin. To him, the almost inevitable terminus of urban living is that every city turns into some variation of Sodom or Gomorrah. Where FitzStephen likes to focus on the games people played when the Thames froze over, Richard focusses on the wide variety of broken people that FitzStephen probably liked to think weren't even there. FitzStephen likens the women of London to the famous Sabines of ancient Rome, while Richard says its full of sex workers.

There was also the third option: that cities had no intrinsic moral value. For Ibn Jubayr, different places were different. Although there is a trend in his account toward praise of multiculturalism (in his view it leads to greater opportunities for learning and trade. He also criticises many cities for treating minorities poorly), he has to balance that with his personal conviction that Christianity was the enemy. He lived in a time when many Christians and Muslims saw each other as being in competition, and a common theme of descriptions of eastern Mediterranean cities is how they do or do not contribute to the author's sense of faith. Although Ibn Jubayr is generally nicer about multicultural places, he is not comfortable with the moral and religious implications of that and worried that the multiculturalism of many eastern Mediterranean cities was eroding the strength of the Muslim faith; that if Muslims and Christians got too comfortable living in the same spaces then the Christians would take advantage or the Muslims would fail to grasp opportunities. This goes so far that he often chastises himself in his descriptions for being "seduced" by the sight of these pleasant metropolises full of Christians, and compensates by discussing how best to invade Sicily.