Place 1/2 cup of the chocolate in a microwave-safe dish and microwave for 25 to 30 seconds. Take out, stir, and if not melted, return to the microwave and microwave for another 25 to 30 seconds until the chocolate is melted. Stir well.
Add the coconut milk and coconut condensed milk into a large bowl and add the melted chocolate as well.
Using a whisk, blend all three ingredients together till well incorporated.
Then, add in the bourbon.
Carefully, pour the mixture into 4 popsicle molds. It might help to use some sort of funnel or spout for easy pouring. If your popsicle molds come with popsicle sticks, then place the molds with the attached popsicle sticks into the freezer and freeze for at least 3 hours. However, if using wooden sticks as the popsicle holders, set the popsicle molds with the boozy bourbon cocoa pops in the freezer for about 45 minutes. Remove them and add the wooden sticks into the middle of the molds. When the popsicle mixture is a bit frozen, the wooden sticks can be set upright and in the middle more easily, and they do not fall to the side.
Then, freeze for 2.5-3 hours.
Dislodge from molds by dipping molds into warm water for a few seconds (15-25 seconds).
Melt the other 1/2 cup of chocolate and dip Chocolate Bourbon Popsicles into the melted chocolate before enjoying.