In a small bowl, combine brown sugar, cinnamon and water. Mix well until wet. It will appear dry at first, just give it a minute of mixing and it will come together well.
Set aside.
Meanwhile, remove the top, bottom and skin/sides of a pineapple. Cut into ½" rounds and remove the center core if desired. I used an apple corer.
Place pineapple rounds onto a pre-heated grill and use a brush to cover one side with a generous amount of the sugar mixture. Close lid and heat for 2-3 minutes before flipping and heating for another 2-3 minutes.
Serve with vanilla ice cream garnished with a pineapple slice and ground cinnamon.