I started out just trying to make a doll that looked like Jack Sparrow. I'm not fond of dressing dolls, so I took far too many shortcuts with him. I used an inexpensive Town Square doll ($10). I stripped the doll down (using nail polish remover to remove the painted features), and then went to work.
I repainted his features with acrylics, re-dressed him, and wigged him. His beard and moustache were a bit of a challenge,but I'm quite happy. His clothing on the other hand was a rushed job, so I'll continue to fiddle with it. Jack was holding a rum bottle, which helped disguise his clumsy hands, but he seems to have dropped it!
I found the boat at my local dollhouse shop for $12, and knew that it would be perfect for Jack. I did a lot of sanding, painting, and even burning to age it, but I'm just glad I didn't have to build the boat! I even managed to add barnacles to the boat bottom, made from painted dollhouse gravel.
I also added props from the three movies to the boat. The original map was seemingly backed with thin wood. I used a heavily textured fabric instead. The pistol is a metal miniature that I adapted slightly and painted. I made the open compass (the black dot sitting on the map) from layers of card. There is also a piece of cursed "Aztec gold" on the map.
I had to make Jack's weather beaten leather hat as well. I'd never made a pirate hat, or a hat from leather before, so I didn't really know what I was doing. I just kept fiddling until it looked right, and bugging my brother (who loves vintage hats) for information. I set the boat on a (aged and distressed) frame from the thrift store to make a display base. Oddly enough, the resin for the "ocean" was the single most expensive part of the whole project, at $20 for the bottle. Altogether, I think I spent about $50 on this project. I've still got a few more touches to add (the sail is still a bit too new, and I'm dissatisfied with Jack's clothing) but I'll wait until I'm really in the mood to fix those things.