Place your mixing bowl and whisk in the freezer for 5-10 minutes to get it very cold.
In your cold mixing bowl, pour in Heavy Cream (1 cup), Rum (1 tablespoon), Vanilla Extract (1 teaspoon), and Granulated Sugar (3 tablespoon).
Whip on the highest speed until peaks start to form, 1-3 minutes, depending your mixer. Store the topping in the refrigerator until ready to serve.
Cut off the sides of the Pineapple (1) with a large knife.
Slice pineapple into about 1/2 inch thick disks. Punch out the hard cores with a cookie cutter or paring knife.
Preheat grill to 350 degrees F (175 degrees C).
Place rings on a baking sheet and brush both sides liberally with Honey (1/4 cup). Grill pineapple rings 5 minutes on each side, flipping only once.
Top pineapple with the rum-infused whipped topping. Sprinkle with Sweetened Shredded Coconut (1/4 cup).