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I'll do some sketching and be back (too bad drawing isn't my strong point lol).

Although I haven't played them, these are finished games:

http://www.boxofmystery.com/games/devils-triangle/
http://www.boxofmystery.com/games/lechucks-revenge/

It would be my intention to do it part-by-part. Sort of how Telltale releases their games (although nowhere near as big a game of course). Part 1 is short, requires 6 rooms and about 12 characters.

MI never had a real pirate hub. But yes, the plot is quite similar to MI1, or at least Act 2. Act 1 and 3 - the beginning and end - are not. Also note that at this stage the game requires two islands, neither of them are Monkey Island (or any other actual island from MI games). But it's much more realistic than the MI1 plot-line since every pirate crew member would be expected to do something, and even if they can't navigate or fight, they could still be a pirate if they could cook or do something else useful. But the plot can always be rewritten, I simply like the present Act 2 plot because it allows for a lot of freedom within it to design puzzles, characters and humour. An alternate one would still have to a. pick up from where act 1 ends, and b. provide suitable mechanisms for the desired game-play environment.

More than a decade ago now I once dreamt of doing a Monkey Island fangame. So I was on holiday the other week, and put pen to paper and designed a game in 2 days that essentially would fulfill the basic requirements: the story I wanted and humour. I've codenamed the game "Manky Island" (yes named after one of the kremlings in the original DKC).

Without giving too much away about the plot, at this stage, it's a standard 3-act story (beginning, middle, end) can be adapted to a 4-part game, and doesn't require the use of any IP thus avoiding legal issues entirely (no MI character names and no MI islands, etc). This fact actually adds to the humour of the game.

Act1: 1 level, puzzels written, requires a total of 6 rooms and at least 10 characters. Story complete. This is intended to be the shortest level.
Act2: 2 levels (or could be combined into one longer level), puzzles designed but not written. Story complete.
Act3: 1-2 levels, not yet written. Story designed but not written.

I'll talk a bit about act2 - act2 involves getting to "manky island" (1st part), which contains the pirate hub, and then joining a pirate crew (2nd part). The problem is that you can't just join a crew with no expertise, and so you have to go around the island and complete training in order to gain a skill that one of the crews may be interested in. Becoming a qualified rower, becoming a qualified banjo player, that kind of thing. True-to-life, the pirate hub is where all the pirates hang out when they aren't at sea and thus the main attractions will be a hotel or two and some pubs! The idea is that you will collect items as you complete training, and you have to complete puzzles to complete the training, and once you've been trained in just about everything a crew might need - navigation, fishing, kidnapping, extortion, etc etc, there are no more pirates left on the island as they've all gone out to sea, that is except for one last crew and thus you join it the only way that any decent wannabe pirate would - via stowaway. There are a lot of ways to have fun with this concept.

If I were to decide to develop this project, would anyone be interested to take part? I'm by no means recruiting at this stage, just explaining my idea, a bit, and wondering if there's interest?