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It depends what are you up to besides skating
I'm into clubbing and raves. Punk. Generally exploring, finding empty buildings. Walking around looking for spots to chill and drink etc.
there are lots of illegal raves in prague, but its hard to find them if you dont know anyone and those comercial ones... well, they all pretty much sucks. but from time to time you can find something interesting at cross or fuchs2. if you are in punk, find hluch crew or dis-beat mafia on facebook. if you like underground metal find kreas. or just go to club 007 , legendary club on strahov hill (also great downhill, if you are not pussy like me).
one 10th of prague houses are abandoned, if you are not afraid of cops, you can get in at least in half of them.