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Stir 2 teaspoons water, 1 teaspoon demerara sugar, and 3 dashes Angostura bitters together in a mixing glass or cocktail shaker until the sugar is nearly dissolved.
Fill a rocks or old-fashioned glass with ice. Fill the mixing glass or cocktail shaker with ice, add 2 ounces bourbon, and stir until well-chilled.
Pour the cocktail through a strainer into the glass. Twist the orange peel directly over the cocktail’s surface, then garnish with the peel. Garnish with 1 to 2 Luxardo cherries if using.