Set up a Multiplayer -> Local Area Network game for Red Death and pick Pirates. If you're close to the water, great! If not, try to get there ASAP. Move all your units in the water. Save your multiplayer game. Hit Shift-Enter to end your turn and keep pressing it until you lose. Go back to multiplayer and load that game. Rinse and repeat until the achievement pops. Shouldn't take more than 3 rounds unless you really had to go far to get to water.