Fill a cocktail shaker and a hurricane glass with ice. Pour all ingredients except the garnish into the cocktail shaker. Shake and strain into the ice-filled hurricane glass and garnish with an orange slice and cherry.
Simple Syrup
Combine equal parts water and sugar in a saucepan, bring to a boil, and stir until dissolved. Let cool before using.
Grenadine
Bring juice to a simmer over medium heat and cook until reduced by half. Reduce heat and add sugar, stirring constantly until dissolved. Let cool before using.