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Prettiest:
Asia: Hong Kong (setting)
Oceana: Sydney (Harbour) or Auckland (setting)
Africa: Cape Town (setting)
Europe: Venice
North America: Vancouver (setting) or San Francisco (setting)
South America: Rio (setting) though Buenos Aires has beautiful architecture
Middle East: Istanbul (architecture, history, setting)
Caribbean: old town San Juan
Ugliest cities:
Asia: Jakarta (too crowded, hot, muggy dirty, though it has nice sections)
Oceana: ??? (not sure) though I found Geelong, Vic not very appealing
Africa: (not sure though have only been to RSA, Egypt and Morocco)
Europe: Novosibirsk
North America: Detroit (though it has some interesting architecture)
South America: Guayaquil (lots of slums, nice river front park thought city is not really safe)
Middle East: (not sure)
Caribbean: Port-au-Prince
Prettiest (based on natural setting, but also built environment, streetscapes and architecture):
Providence
San Francisco
Oakland
Berkeley
San Diego
Philadelphia
NYC
Los Angeles
Patzcuaro, Mexico
Sacramento
Ugliest:
San Jose (sorry, SJ, I like you a lot, and downtown is actually very pretty...but you can't compare to other cities in terms of your underwhelming looks overall and large swaths of suburbia.)
Los Angeles (LA gets listed here as well as in prettiest, because while I love the setting, downtown, and the denser areas, there are still plenty of ugly sprawling suburban areas too, not to mention tons of freeways slicing it all up)
Morelia, Mexico
Tijuana, Mexico
Ensenada, Mexico (Ensenada probably wins the ugly competition)
Vacaville, California (the epitome of sprawl and cookie cutter homes. The natural setting really is pretty amazing though)
I've never been to Detroit, but through pics i've seen I find that place to be beautiful, but of course extremely neglected. There really is some amazing architecture in Detroit, and their skyline is one of the more unique and impressive ones in the US. Yeah there are plenty of extremely run down areas that really have no beauty left in them, but the bones are still there... I would be cool to go back in time and see what the place was like when it was flourishing.
Of the places that I have lived.......
UGLIEST: ATLANTIC CITY NJ
PRETTIEST: TOUL, FRANCE
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