Reading through this thread made me realize that I haven't been many places...
NYC: I was shocked that the sidewalks were not as crowded as I thought they would be. I was also surprised that I couldn't find a decent cup of coffee near where we were staying by Times Square.
I'm pretty easily impressed so most things meet my expectations. Although, I still can't get over how tall the Sears Tower is. I see it almost everyday and I am still in awe.