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In large microwave-safe bowl, melt Candy Melts candy according to package instructions. In small microwave-safe bowl, heat 1/3 cup cream until steaming, about 30 seconds. Add to melted candy and stir until well combined. Cool slightly.
In small bowl, whip 2/3 cup cream, confectioners' sugar and 1 tablespoon rum to soft peaks; set aside.
Blend sherbet, remaining 1/4 cup light rum, and coconut candy mixture in blender until smooth and well combined.
Pour milkshake into 4 glasses. Skewer pineapple half-rings and maraschino cherries onto toothpicks. Top with whipped cream and fruit skewers.