Each territory so far is going to be a group of 5 or 4.
I'll most likely do some prettying up later, but its just a rough draft.

http://imageshack.us/photo/my-images/692/testingn.png/

What do you guys think?

Update 1
http://imageshack.us/photo/my-images/59/testingz.png/

I may be showing my ignorance here but what's it supposed to be of?

A map, perhaps 2v2. I'm thinking of about 4 choke points between the two islands. I might separate them into even smaller territories if I have the time and motivation.

I'm aware it's a map of two islands.

I was assuming it was of a real place and thus wondering where it was. Sounds like it is not however.

Oh, its just fictional. I did take a few random islands for their shorelines though.