What now?

Ok I have done this fisher mans quiz, I have gotten caught trespassing at light house, I have had bricks fall on my head, but what now? I'm doing the jr. So the things on the notes (on computer) say figure out who trashed Katies boat and figure out the messages in the bottles. But what I really need to know is how to be able to play chess with Holt! How do I do that! I mean how to I get to be able to!
Thanks!