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In a medium saucepan over medium heat, combine the can of coconut milk but SAVE 2 TABLESPOONS and reserve them for now.
Whisk in the cocoa powder, maple syrup and water. Whisk over medium heat until evenly combined, then turn the heat off and continue to gently stir until all the air bubbles are gone. No bubbly fudgesicles, please! Allow to cool briefly.
Meanwhile in a small bowl, combine the reserved coconut milk with the vanilla extract (and a teensy bit of extra maple syrup if desired) until smooth.
Prepare your popsicle molds, then drizzle the vanilla coconut milk combination evenly into each. Place this in the freezer for about 5 minutes.
Take the popsicle mold out of the freezer and evenly pour the hot cocoa liquid into each mold. Top your popsicle mold and insert the wooden sticks, then return to the freezer and allow to set up for at least 4 hours or overnight.