Blend pineapple chunks, ice, coconut milk, lime juice, and rum in a blender or food processor until combined and smooth.
4 cups pineapple, 1 1/2 to 2 cups ice cubes, 4 ounces coconut milk, 3 ounces rum
Taste test and if you'd like it sweeter, and add honey or simple syrup a little at a time, blending again to combine.
Simple syrup
Pour into glasses and garnish with cherries, pineapple chunks, and/or lime slices and serve immediately. Enjoy!
Maraschino cherries
Notes
Tip: Taste a piece of pineapple before making the drinks. If you find that the pineapple isn't very sweet, then you'll know ahead of time that you may want to add a sweetener.