Chef’s Note: To pick a ripe pineapple, it should have a light, sweet pineapple fragrance, especially at its base.
Cut off the top and bottom of the pineapple using a sharp chef's knife. Stand the fruit upright and cut off the skin, following the curve of the fruit. Remove any remaining hard brown spots, or "eyes," with a paring knife. Slice the peeled pineapple crosswise into 6 to 8 rounds depending on the size of pineapple. Use a small round cookie cutter to punch out the core of each slice or cut out with a paring knife.
In a small bowl, add sugar and five spice and mix well. Place pineapple rings on a large baking sheet and sprinkle the sugar mixture on each side of the pineapple rings; let marinade for 10 minutes.
Spray both sides of the pineapple rings with non-stick cooking spray and grill on high heat for 2 minutes per side until lightly charred. To serve, place a grilled pineapple in a bowl and top with coconut ice cream.