Add bourbon (2 oz), dry vermouth (1/2 oz), amaro (1/4 oz), maraschino liqueur (1/4 oz), simple syrup (1/4 oz), orange bitters (2 dashes), and Angostura bitters (1 dash) into a mixing glass.

Fill the mixing glass with plenty of ice (large cubes work best). Stir gently for 20–30 seconds until the mixture is well chilled and properly diluted (about 10–15 full rotations with a bar spoon).

Discard the ice/water from the chilled rocks glass and place a large ice cube or sphere into it.

Strain the stirred cocktail into the prepared rocks glass over the single large ice cube using a fine Hawthorne or Julep strainer to catch small shards.

Garnish & Serve

Express the oils of the orange peel over the drink by holding the peel skin-side down about 3–4 inches above the surface and giving it a firm twist to spray the oils onto the cocktail.

Rub the expressed peel around the rim of the glass, then drop the peel into the drink or rest it on the rim. Optionally, add a Luxardo cherry on a pick and rest it alongside the peel.

Serve immediately. Sip slowly to appreciate the layered interplay of bourbon warmth, herbal amaro, maraschino sweetness, and bright citrus oil.