Lay pineapple slices on a baking sheet and place a maraschino cherry in the center of each one. Add a small amount of water to the center of each pineapple; cover and freeze, 8 hours to overnight.
Pour pineapple juice, orange juice, cream of coconut, light rum, dark rum, and frozen lemonade concentrate into a clean, 1-gallon container with a lid. Shake punch to combine and pour into a punch bowl. Add the frozen pineapple-cherry garnishes.