If desired, chill the old fashioned glass by filling with ice and water while you mix the cocktail. Prepare a large ice cube or several fresh ice cubes and set aside.

Measure and combine ingredients

In a mixing glass or shaker, pour 2 oz bourbon, 1 oz sweet vermouth, 1 oz amaro, 0.25 oz simple syrup, and 2 dashes orange bitters.

Add ice and stir

Add enough ice to the mixing glass to fill it. Using a bar spoon, stir the mixture briskly for 20–30 seconds (about 15–20 revolutions) until well chilled and slightly diluted.

Prepare serving glass

Discard the chilling ice/water from the old fashioned glass if you chilled it. Place the large ice cube (or fresh ice) into the serving glass.

Strain and garnish

Using a strainer, pour the chilled cocktail into the prepared rocks glass over the ice. Express an orange peel over the drink by holding it skin-side down and giving it a firm twist to release the oils, then rub the peel around the rim and drop it into the glass as garnish.

Serve

Serve immediately. Sip slowly to enjoy the balance of bourbon, sweet vermouth, and amaro with the citrus aroma from the orange peel.

Tools

Use the jigger to measure spirits and the bar spoon to stir. Use the strainer when pouring from a mixing glass. A peeler or knife will produce a clean orange peel for garnish.