Step 1

Place the bourbon, sweet vermouth, orange juice, unsweetened cranberry juice, and simple syrup in a cocktail shaker. Fill it with ice and shake until cold.

Step 2

Strain the drink into an ice-filled lowball glass. If desired, garnish with fresh or frozen cranberries and rosemary sprigs.

Step 3

Add 1 1/2 cups bourbon, 1 cup sweet vermouth, 2 cups orange juice, 1 cup unsweetened cranberry juice, and 1/2 cup simple syrup to a pitcher. Add 2 handfuls ice and stir until cold.