For the Spiced Simple Syrup
Add sugar and water to a saucepan and bring to a simmer over medium heat. Add in star anise pieces and vanilla extract and stir until sugar is completely dissolved. Let cool completely before adding to cocktail.
For The Cocktail
Add ice to a cocktail shaker.
Pour bourbon, cranberry juice, freshly squeezed lemon juice and spiced simple syrup into the cocktail shaker.
Fill a rocks glass with ice, we recommend an ice sphere or other large cut of ice.
Pour the drink over the ice.
Garnish with a slice of orange, a sprig of rosemary, and cranberries and enjoy!