Try it anywhere on your property, assuming you don't have people staying there to be embarrassed in front of. Also, move any breakable stuff away. I once broke a vase skateboarding in my living room.
I don't mind doing weird stuff in public when I'm with a friend, but alone, I feel weird.
I was going to try bench jumping at a park, and there was a guy about my age (17) playing on the playground equipment. I walked past and he was sitting on the swing, so it felt kind of awkward if I were to just run up and try to jump over the nearby bench, haha.
I wouldn't judge anyone else if they did some stuff I'd be shy to do in public, in fact I would probably think they were interesting and cool. I wonder if other people would view me the same way, and most people a trapped because of this false concept of a cultural norm that others are judgmental, and if the people who take "social norms" too seriously are actually rare, and are deluded, uptight, and their opinions mostly don't matter.