My favorite is when he got caught masturbating in public and responded with "If only it were as easy to banish hunger by rubbing the belly." Or when Plato was teaching a class and defined a man as a featherless biped, and Diogenes brought a plucked chicken to the class and said "Behold, Plato's man!"
I like exploring old buildings like churches and hotels. I feel like architecture has been optimized so much to fire codes that most modern buildings have pretty boring layouts. But older buildings are completely batshit in their designs sometimes. Like woah there's a second little staircase down here that goes to a single room not accessible by anywhere else, or just random little hallways to nowhere. Also secret little closets everywhere, it's way more fun.