In small bowl, stir dulce de leche and enough milk with wire whisk to make a smooth, pourable sauce.
Cut each banana in half lengthwise and then crosswise. In each of 4 stemmed dessert glasses or bowls, place 2 banana quarters along outer edges. Top each with 1 scoop vanilla ice cream and 1 scoop chocolate ice cream. Spoon dulce de leche mixture evenly over ice cream. Top with whipped cream, peanuts and cherries. Serve immediately.