Siena to Berlin
I thought a city couldn't feel and look older than Florence until I went to the nearby medieval cities of Siena and San Gimignano. The two are built on hills so they have lots of steep, winding roads and views of the nearby landscape. On the other hand Berlin has an incredibly modern and vast feel. I understood that the far majority of the buildings would have been built or rebuilt after World War Two, but quickly realized that many of the city's office buildings, government buildings, and residential areas are from after the fall of the Berlin wall. A city with an immense history yet most of the buildings I went in were constructed in the 90's and later.