Rim two glasses with honey or simple syrup, then dip the rims into toasted coconut flakes to coat, and place glasses in the freezer for 5 minutes.
In a high-speed blender, combine the pineapple chunks, coconut cream, coconut water, pineapple juice, and honey.
Add the ice cubes to the blender and blend on high speed for 45-60 seconds until completely smooth and slushy.
Taste and adjust sweetness if needed by adding more honey, then blend again briefly to incorporate.
Pour the frozen mixture into the prepared chilled glasses, filling them to the top.
Garnish each glass with a pineapple wedge and maraschino cherry, then serve immediately with a straw.