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Bring milk to a simmer in small saucepan over medium heat. Whisk in sugar and cocoa powder and stir until no lumps remain. Stir in chocolate chips and vanilla and cook, stirring occasionally, until the chocolate is completely melted. Stir in Rumchata, then turn off heat. Pour caramel into a small dish. Dip cups in the caramel to coat the rim. Pour hot chocolate into each glass, then top with whipped cream, a sprinkle of cinnamon sugar, more caramel, and a cinnamon stick.