There's a break in the railing that lets you do so here, so go ahead. Also on the roof, you'll find a man who basically tells you that, troublemaker he is, Will often jumps down off high places to startle people.
There's something called a 'Red Jewel' here. (Also, talking to Gaia while not at full HP will give you a full heal.) Once you return to the church's roof, go to the left side of the bell tower and walk inside, then press Attack. If you go inside, the spirit of Gaia will give you some exposition on this. Only Will can see these 'Dark Portals' no one else notices them. On the church roof, you'll notice a sparkle.
It's down near the docks.) Once you gain control of Will, climb the staircase. (Well, actually, one, named 'Lance' stays behind to remind you where the hideout is. Will's three friends leave to go to their 'Hideout' and tell Will to meet them there later. Will's interior monologue tells you the backstory, and shortly after, class lets out.
