I just got another vivid memory of some other game I remember playing fairly often.
I believe you were playing as a pirate. I think I remember you being able to travel around a map and barter or something at other places, although I can't really remember much else.
Its pretty vague... But it was kinda like a strategy adventure game with a neat art style. I swear it wasnt any of the Monkey Island games though.
Ok so I went and looked it up and I found it: Tradewinds! Or maybe it was the second one? Either way, the screenshots I found rung a bell and I got the name.
It was another game in the WildTangent launcher that I remember playing a whole bunch too.