Add 1 cup cold brewed coffee, ¼ cup half and half, 2 cups ice, 1 teaspoon vanilla extract, 2 tablespoons granulated sugar, and 3 tablespoons chocolate syrup to a blender.
Blend until the mixture is smooth and creamy.
Divide the blended coffee evenly between 2 serving glasses.
Top each drink with ¼ cup whipped cream and drizzle additional chocolate syrup over the whipped cream.
Serve immediately while cold.
Notes
If the mixture is too thick, add a little more brewed coffee or half and half and blend again until it reaches your desired consistency.If the mixture is too thin, add more ice and blend again.