Caramelize brown sugar in a non-stick pan. Add pineapple slices and coat well. Cook till pineapple slices turn soft. Remove from heat and cool to room temperature.
Reserve some caramelized pineapple slices and combine the remaining with ice cream and milk in a blender jar and blend well.
Pour the drink into individual martini glasses. Cut reserved caramelized pineapple slices into wedges.
Garnish the glasses with caramelized pineapple wedges and serve chilled.