In a small pot over medium heat, combine the sugar, water, rosemary, and sliced ginger. Stir occasionally for about 5 minutes or until all the sugar is dissolved and the mixture is slightly reduced.
Remove from the heat, stir in the vanilla. Transfer to a small bowl, and place in the refrigerator to chill.
Once the syrup has chilled (about 20-30 minutes), discard the rosemary and sliced ginger. Fill a rocks glass with ice.
To the glass, add the bitters, vodka, triple sec, rosemary syrup, and cranberry juice and stir.
Garnish with cranberries, an orange wheel, and a rosemary sprig and serve immediately.
Notes
Make the syrup ahead for easy entertaining: The rosemary-ginger syrup is where all the magic happens, and it actually tastes even better after it’s had time to rest in the fridge. Make a batch a day or two before your party, tuck it into a jar, and you’ll be just a quick shake away from beautiful holiday cocktails all night long.
Adjust the sweetness to your crowd: Using unsweetened cranberry juice keeps this cocktail nicely balanced, but everyone’s sweet tooth is a little different. If you’re serving guests who like things on the sweeter side, add an extra splash of syrup or use a mix of unsweetened and sweetened cranberry juice until it tastes just right.
Let the garnish do some of the work: Don’t skip the rosemary sprig, cranberries, and orange slice—they add aroma, color, and a little “wow” factor with almost no effort. Frozen cranberries are especially handy here; they look gorgeous, help keep the drink chilled, and don’t water it down like extra ice.