Using a vinyl wrap would absolutely destroy the tone of the drum.

If you're using an Ambassador-style head (slightly rough surface) then markers would do a passable job, I think. A Pinstripe head would be too slick to hold the ink, and would require a silk-screening job of some sort. Setting the screen would be a problem - you can't really heat a plastic head up to dry things out.

A good-old fashioned hide head would be easy to dye, but present constant tuning problems.

Good luck, and let us know what works out for you!

Slainte,