Step 1: Fill a highball or old-fashioned glass with ice.
Step 2: Place 4 ounces pineapple juice and 2 ounces coconut rum in a cocktail shaker.
Step 3: Fill the shaker halfway with ice, seal, and shake until the outside of the shaker is very frosty, about 20 seconds.
Step 4: Pour through a fine-mesh strainer into the glass.
Step 5: Slowly pour 1/2 ounce grenadine into the center of the glass letting it settle on the bottom.
Step 6: Garnish with 1 fresh pineapple wedge and a maraschino cherry.
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