Chill two tall glasses in the freezer for at least 30 minutes.

In a blender, combine the frozen strawberries, fresh strawberries, lime juice, simple syrup, and rum (if using). Blend until a thick, smooth puree forms.

Divide the strawberry puree evenly into the bottom of the chilled glasses. Use a spoon to smear a little puree up the inside walls of the glasses. Set glasses aside.

Rinse the blender pitcher clean.

Add the frozen pineapple chunks, pineapple juice, Cream of Coconut, and rum (if using) to the blender. Blend on high until thick and incredibly smooth. Add crushed ice only if the mixture is too thin.

Slowly pour the pineapple-coconut mixture directly into the center of the strawberry puree in the glasses. The red puree will flow up the sides.

Top each glass generously with whipped cream. Garnish the rims with a fresh strawberry and a pineapple wedge. Add a straw and serve immediately.