I think there was never a desire to decide what was “the most beautiful city in the world” but simply an invitation to list beautiful places we had been (and not, as some here felt inclined to do, criticize places we apparently hadn’t). The acrimonious comparison of New and Old world cities inspired me to translate the first paragraph of the chapter about Sao Paolo in Claude Levi-Strauss’ masterpiece Tristes Tropiques*. A malicious wit [my note: I believe he refers to Oscar Wilde] once defined America as a country that has gone from barbarism to decadence without knowing civilization. That formula could be applied more accurately to the cities of the new world: they go from freshness to decrepitude without any period of antiquity. A Brazilian student came to me in tears after her first voyage to France: Paris seemed so dirty to her, with its blackened buildings; whiteness and cleanliness were the only criteria she had for judging a city. But the vacations away from time we are invited on by the monumentality, the ageless life that characterize the most beautiful cities, become objects of contemplation and reflection, and no longer simple instruments of urban function -- American cities never attain. In the cities of the New World, whether new York, Chicago or Sao Paolo, it’s not the absence of ancient landmarks that strike me : their absence is an element of their signification. But contrary to those European tourists that pout because they can’t add another 13th century cathedral to the list of monuments they’ve bagged, I’m overjoyed to adapt myself to a system without the dimension of time, interpreting a different form of civilization. he continues with a comparison that basically shows that there is no right answer to the question in this thread header. this took place in the thirties; these days Europe has caught the renovation bug, and the York Minster, the Louvre and even that mountain of coal the Kölner Dom are now as sparkling as the day they were born. I’m of two minds if this is a good thing: the Sistine chapel is obviously much prettier now, but is it as impressive? The age and history represented by the dust and soot perhaps were as important, and had as much to say to us, as the allegories represented by the mastery of Michelangelo. I have seen a great many monuments all over the world, but in the Grand Place in Brussels, under a double mantle of lowering dusky sky and the veneer of centuries, I felt a weight of history, like the pressure of being under 5 meters of water. This feeling is less and less common when visiting the great monuments of Europe. Contrarywise, there are places in the New World, places that were once important and are now backwaters, that have become vivid reminders of days (admittedly only just) gone by and I think Valparaiso (i've never been) may be one of them. * this Levi-Strauss had nothing to do with blue jeans; he was (he died this year at the age of 101) one of the leading minds, and Tristes Tropiques one of the most important works of the 20th century. A work almost worth learning French for all by itself! as translations go Weightman is decent but Russell (the only one available online) is ghastly. Better to avoid Levi-Strauss completely than get an idea so false about his style or theories.