Special equipment: a tropical drink umbrella, straws, hurricane glasses or fun equivalent, cocktail shaker
Preheat the oven to broil.
Pour the sugar in a shallow bowl and dip the orange slices and pineapple wedges, coating one side of each with the sugar. Transfer the fruit to a sheet tray, sugared-side up, and place under the broiler to caramelize, about 5 minutes.
Fill a cocktail shaker with ice and pour in the orange juice, pineapple juice and rum. Cover and shake. Strain into an ice-filled hurricane glass. Garnish with a caramelized orange slice, pineapple wedge, cinnamon stick and umbrella. Reserve the remaining fruit for snacking or more drinks.
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