PLACE evaporated milk, coconut cream, pineapple juice and rum extract in blender container; cover. Blend until well combined. Pour mixture into pitcher; refrigerate until ready to use.
TO SERVE: Place half of beverage and 3 cups ice in blender container; cover. Blend until smooth. Pour into serving glasses. Repeat with remaining beverage and ice. Garnish glasses with pineapple wedges and maraschino cherries.
* NOTE: 2 tablespoons rum can be substituted for the rum extract.