Congrats on being allowed to participate with this one :] I didn't think the local seadogs would have admitted an entry posted as late as two days after the deadline, but I guess this goes to show how wrong we are in our assumptions regarding pirates!
You've certainly got a nice idea there, refitting the prison and turning it into a fun place to hang around. Some of the details are definitely very succesful, such as the gallows rope used as a hoop and the "newly-invented" food-cutting machine. I must admit though that I would have liked to see more of those and perhaps if you'd entered the contest a bit earlier, you could have asked C-P members what torture devices / prison equipment they'd like to see refurbished and used peacefully in these peaceful times. After all, that's what the Creative Critic part of this contest is all about and that's what it makes it so much fun for the participants! Off the top of my head, you could for example have had an isolation chamber turned into a freezer compartment - such additions would have turned this MOC into a much more lively place. So I'm not sure if you've managed to use 100% of the potential that you had with this wonderful idea of yours, but it's still a very nice entry.
However, some of the details featured here could have used more work - such as the staircase which you could easily have kept in this brick-built form, as long as you'd placed it along the wall. As it is now, it looks very unstable and a bit out of place - and seeing as it's one of the main interior features that viewers' attention is focused on, I'm thinking that you should have tried and added more details and realism to it.
The same applies to the flames, two of which seem to come pretty much out of nowhere (the ones on both sides of the door). Coming up with a couple of nice lanterns could have made a huge difference there and would have definitely been very eye-pleasing. And as to the rooftop, it has been turned into a nice garden, but definitely not a greenhouse - and having precisely a greenhouse up there would have been such a cool idea. I guess you didn't really have the time to include that, but I did enjoy your idea, pity you didn't take it all the way.
Good luck in the competition - you've certainly had some in having this entry admitted :)