This seems like a problem that's not really related to drawing the route.
You want to find the shortest path from one point to another, given certain criteria - where you can and cannot move, for example. I don't see this problem as something you can solve with drawing, but with actually calculating the different possible ways and then compare them. When you have decided which is the best route. Drawing is pretty simple.
How you would go by deciding I'm actually not sure - sorry 'bout that. But you should probably have a look at some shortest path algorithms. But that probably means you have to represent the underlying image as a pattern, or a series of nodes but graphical problems are not my cup of tea, so I'm not really sure how.
Just a side note - If the number of possible ways of getting from point A to point B are great, this can become a computational problem, and you have to make sure that the iPhone can manage.
(this should probably be a comment somewhere, but since I can't yet and I still wanted to share my two cents, it became an answer.)
Edit:
I just thought of really naive aproach! - for fun mostly, but I couldn't keep myself from posting.
Suppose you have a representation of the image. What parts can't be traveled on and what parts can be. Each pixel that can be travelled on is represented by a 1, and every other pixel is represented by a 0. Thus the pixels represented by 1s can be seen as nodes on which we can travel.
Each node can reach, at most, 8 other nodes - the adjacent pixels. And the weight of travelling between any two nodes could be set as 1. But we have to account that travelling in a diagonal is a greater distance so that weight should be sqrt(2).
Now we have a great bunch of nodes - each with weights in between them. From here we can apply a djikstra-algorithm to find the best route. (maybe some other algorithm is more beneficial at this point - but djikstras is the only one I'm familiar with).
hum, wonder how bad of a solution this would be. ... again, you probably don't want this solution...
EDIT 2:
I will say this again that this is probably not the best way to do this! You should seriously ask someone with more experience in algorithms and in graphical problems. - This was something I thought of at 3am and was mostly for laughs.