When I first start a project like this I try to avoid the temptation to scour the internet to see what others have done with a similar concept. I'm not very good at resisting temptation, and after a brief search I found several different takes on ukuleles looking like pineapples--there is even a type of ukulele called a "pineapple ukulele," based on its shape, not necessarily its exterior paint job.
(NOTE: use caution scouring the internet using the abbreviated "uke" as a search term...)
What follows is my take on the pineapple ukulele. In the end, this was a bigger undertaking than I originally thought, and it involved a lot of trial and error as far as getting the pineapple design down. But oh well, enjoy!
Step 1: Headstock Becomes the Crown
Anyways, since the headstock would only need four tuning pegs, I wanted to use that extra space to make a design that would resemble the crown of a pineapple. I traced the rough design onto the headstock, and on the back I marked the tuning peg strip as well.
Using a dremel, I cut the metal tuning peg strip so that there were four, separate tuning pegs. Then, I used a small handsaw to cut the curves of the leaves into the headstock. After all the cutting, I sanded the entire headstock smooth, using a wood rasp and a series of different grade sandpapers.