squatters are the hot shit right now, just go find some rickety old mansion in the hills, chances are there will be some hipster gypsies living there already so bring some beer. downtown isnt very interesting, i would just hangout in the pearl district and the Saturday market are some chill places, also checkout the east side like Mississippi ave, there's a bomb Mexican place called por que no. hot-lips pizza is everywhere and there good too.
And stay away from china town, crazy shit goes down there at night