Cut and core the pineapple into even slices. Place them on the pan and give them a sprinkle of cinnamon and sugar. Next transfer the pineapple onto the grilling tray and keep it under an open grill for about 15 minutes.
Remove pineapple from grill pan and place directly on the grill. Leave the pineapple of the grill for approximately 5-10 minutes each side or until grill marks are visible.
Transfer pineapple to plate and serve with a slice of pound cake, whipped topping, ice cream, and caramel! Serve immediately.