For the hot chocolate: heat milk over stovetop and bring to a boil.
Remove from heat and stir in cacao, vanilla and bourbon; pour into mug.
For the whipped cream: open the can of coconut cream and drain all of the liquid from it; pour cream into a bowl.
Add powdered sugar, vanilla bean and extract and mix together, preferably with an electric mixer.
Pour whipped cream into a bowl and place in the freezer. The longer it freezes the more like "cool whip" it'll become, but it should be ok to use after 20 minutes or so.
Top hot chocolate with whipped cream and enjoy!