The Story of Brewster Chipptooth, by Carmel Games, is a short point-and-click adventure about a scrawny scallywag who decides he's done with the yo-ho-ho-ery and wants to find a legendary treasure to give to the poor. Of course, he's on his own, since the pirates he's just abandoned aren't that keen to help him out, but luckily he's got you on his side! To play, just click to interact with people and objects when the icon changes as you pass over them, and remember to try combining items in your inventory when you get stuck. Most Carmel Games titles are a blend between puzzles that are straightforward, and those that are, well, kinda silly. Though The Story of Brewster Chipptooth reuses several puzzles and characters from previous games, it's still an appealingly weird little game that'll give you a taste of the pirate's life without ever needing to leave your chair.
I think, if you spend your dubloons in the wrong order, you can end up in an unwinnable situation?
I did indeed miss something. Ahem.
Yeah, I think a lot of people had that happen to them...
Yes, it *seems* like it's possible to get into an unwinnable situation, but it actually isn't, because getting the last doubloon does not depend on how you spend your other doubloons. You just need to do a little bit of backtracking, because things change after you do stuff.
Very sketchy walkthrough:
Update