Measure out 1 cup of fresh pineapple chunks and place them into the blender.
Add 1/2 cup of coconut milk to the blender with the pineapple.
Pour in 1 1/2 oz of white rum into the blender.
Add 1 cup of ice cubes to the blender to achieve a frosty consistency.
Optional: add 1 tablespoon of simple syrup for extra sweetness.
Blend all ingredients on high until smooth, thick, and frosty, usually about 30-45 seconds. The mixture should have a creamy, uniform texture with no large pieces remaining.
Pour the blended Piña Colada into chilled glasses. Garnish each with a pineapple wedge and a maraschino cherry for a colorful presentation.