Charred Cinnamon Pineapple Old Fashioned: A Tropical Twist on a Classic Cocktail

Heat a grill pan or regular pan over medium-high heat.
Place the pineapple slice on the pan and allow it to cook for about 2-3 minutes per side until you get a nice char and caramelization. Once charred, remove from heat and set aside to cool slightly.
Prepare the Cocktail Base:

In a mixing glass or small cocktail shaker, combine the bourbon, simple syrup, bitters, and ground cinnamon (if using). Stir gently to combine.
Add a few ice cubes to the mixing glass and stir the ingredients for about 20-30 seconds to chill and dilute slightly.
Assemble the Drink:

Place a large ice cube or several smaller cubes into a rocks glass.
Strain the bourbon mixture into the glass over the ice.
Add the Charred Pineapple:

Cut the charred pineapple slice into smaller pieces (or leave it as a whole slice, depending on your preference).
Place the pineapple into the glass as a garnish. For added aroma and flavor, you can add a cinnamon stick or a light sprinkle of cinnamon on top of the drink.
Garnish and Serve:

Express the oils from an orange peel by twisting it over the glass and then drop it into the drink as a garnish.
Serve immediately and enjoy the tropical flavors of this smoky, spiced Old Fashioned!
Serving and Storage Tips