Combine SKYY Infusions Pineapple and pineapple juice in cocktail shaker with ice. Strain over fresh ice into a clear Collins glass. Combine softened orange sherbet and ice in a cocktail shaker and shake vigorously. Strain, and pour over bar spoon to layer in the rocks glass. Then, combine simple syrup and milk in cocktail shaker and shake vigorously. Layer milk mixture on top of sorbet mixture.