Preheat your broiler to high. Line a small baking sheet with parchment paper. Add pineapple to the lined baking sheet. Sprinkle the pineapple cubes with the brown sugar. Place under the broiler for 10 minutes until dark golden. Flip and char the other side for another 5-7 minutes.

Add ice, charred pineapple, pineapple juice, tequila, lime juice and simple syrup to a blender. Press the crush ice setting and blend the mixture until it has the perfect frozen margarita texture.

Pour into glasses rimmed with salt or chile lime seasoning. Garnish with lime wedges, pineapple slices, or fresh mint or all of the above.