Combine 1/2 cup dark rum and next 4 ingredients; pour over crushed ice. Top each serving with 1 tablespoon dark rum. Garnish with a maraschino cherry and a pineapple wedge.
*In testing, we used 1/2 cup Cavalier Extra Old Antigua Rum to mix punch and 1/4 cup Myer's Rum, divided, to top servings.
