pirate based adventurer hook or map?
Design, map, or give an overview of a ship for PCs or NPCs.
Pirate/ship adventure, with or without map... even better, I have a map you can use as part of the contest if you wish.
Pirate themed magic items.
I think the contest should be, how fast you can send me the PDF...I'll time you.
Write a pirate sea diddy.
I like "Write a pirate sea diddy..."But how about sing and record it and send it in, too? Then you could post the winning recording!