Step 1: Prepare Your Mixing Glass

Fill a mixing glass with ice cubes to chill the ingredients and maintain the drink’s smooth consistency. Chilling the glass beforehand can enhance the drinking experience.

Step 2: Add the Bourbon

Pour 2 oz of bourbon into the mixing glass. Bourbon serves as the foundation of the cocktail, delivering a smooth, caramelized depth with hints of vanilla and spice. Choose a high-quality bourbon for a refined and well-rounded taste.

Step 3: Incorporate the Red Wine

Add 1 oz of red wine to the bourbon. The red wine introduces a layer of fruitiness and tannins, enhancing the complexity of the drink. Opt for a full-bodied wine like Cabernet Sauvignon, Merlot, or Zinfandel to complement the boldness of the bourbon.

Step 4: Add the Cherry and Simple Syrups

Pour in 1 oz of cherry syrup to infuse the cocktail with a rich, natural cherry sweetness. If you prefer a more tart flavor, use cherry juice instead. Follow up with 1/2 oz of simple syrup to enhance the smoothness and balance out the bold flavors. Adjust the amount based on your sweetness preference.

Step 5: Add the Bitters

Drop in 2 dashes of bitters, which help to round out the flavors and add subtle spice and aromatic complexity. Traditional Angostura bitters work well, but cherry bitters can elevate the drink’s fruitiness.

Step 6: Stir Well

Using a bar spoon, stir the ingredients gently for about 30 seconds to ensure they are well mixed and properly chilled. Stirring (rather than shaking) maintains the smooth texture of the cocktail.

Step 7: Strain into a Glass

Strain the mixture into a chilled rocks glass over a large ice cube. Using a large ice cube slows dilution, allowing you to enjoy the drink’s full-bodied flavor longer.

Step 8: Garnish and Serve

Garnish with a luxardo cherry or fresh cherry on a cocktail pick and a twist of orange peel. Express the orange peel over the drink by twisting it slightly to release its natural oils, then drop it into the glass for an added citrus aroma. Serve immediately and enjoy!