Wash and dry the pineapple. Cut the top and bottom of the pineapple off. Peel the pineapple with a knife, saving as much of the skin. Set skins aside. Boil 5 cups of water in a medium pot or saucepan. Add pineapple skins, rice, and cinnamon. Cook 25-30 minutes or until rice is cooked and pineapple and cinnamon are fragrant. Remove from heat and cool for 10 minutes. Remove pineapple skins and cinnamon sticks. Transfer rice and water to a separate bowl.
Add evaporated milk, sugar, vanilla and pineapple meat to your liking to the rice and water. Stir until combined. Transfer to a blender and blend 30-45 seconds or until smooth. Pour into a glass and garnish with pineapple chunks. You may chill the arroz con piña in the fridge or add ice cubes to cool instantly.