Begin by combining the pineapple juice and cream of coconut in a high-speed blender. Add the ice over the liquid to ensure an even blend. Blend on high for 30 to 60 seconds, or until the mixture is completely smooth and frothy.
Once blended, pour the creamy tropical mixture evenly into 3 to 4 serving glasses. The recipe yields approximately 5 cups of piña colada, which divides into around 10 ounces per glass if serving four.
To serve, top each glass with a fresh pineapple wedge and a glossy maraschino cherry. Add a cocktail umbrella for a festive finishing touch and serve immediately while chilled and frosty.