Place first 5 ingredients in a blender; process 1 minute or until smooth, scraping sides as necessary. Pour into 5 glasses. Garnish each serving with 1 fresh cherry, if desired.
Skip the Dairy Omit the ice cream, milk, and sweet baking chocolate. Use equal amounts of chocolate almond milk ice cream and almond milk instead; replace the sweet baking chocolate with an equal amount of grated dairy-free chocolate.