Pour the chilled water, evaporated milk, sweetened condensed milk, and vanilla flavoring into a blender. This forms the base of your creamy banana drink.
Peel the fully ripe bananas and add them to the blender in large pieces to help the blending process. Then add the ice cubes to the blender. If your blender is too full, feel free to blend in two batches for easier handling. I find blending in smaller portions can make the texture even smoother.
Blend the mixture on high speed for 1-2 minutes, or until everything is smooth and creamy. Check that the bananas are fully blended and the ice is crushed evenly.
Pour the drink over extra ice in glasses, or transfer it to a pitcher or bottle and refrigerate for 30 minutes to 1 hour until cold. This drink is best served well chilled.
Before serving, garnish each glass with a light sprinkle of ground cinnamon for extra flavor, if desired. I like to add a little more cinnamon for a delicious aromatic touch.