Add 2 oz WhistlePig (or your preferred rye/bourbon), 0.75 oz sweet vermouth, 0.5 oz amaro, 2 dashes Angostura bitters, 1 dash orange bitters and 0.25 tsp simple syrup (if using) into a mixing glass filled with plenty of ice.

Stir

Stir vigorously for 20–30 seconds (about 20–30 full spoon rotations) until the mixture is well chilled and properly diluted — the glass should frost slightly and the cocktail will take on a silky texture.

Prepare glass

Place a single large ice cube into a chilled rocks glass.

Strain

Strain the stirred cocktail over the large ice cube into the prepared rocks glass using a hawthorne or julep strainer.

Bourbon float (the 'piggy back')

Using the back of a bar spoon, gently pour 0.25 oz of a higher‑proof bourbon over the back of the spoon so it floats on top of the cocktail. This creates the signature 'piggy back' — a burst of aromatic heat and extra bourbon on each sip.

Garnish & Finish

Express the oils from an orange twist over the surface of the cocktail by holding the twist skin side down and giving it a quick squeeze/press above the drink. Rub the rim of the glass with the twist and drop it into the drink or rest it on the rim.

Optional: skewer and add a Luxardo cherry for a classic touch.

Serve immediately and advise the drinker to take a sip through the floated bourbon so they experience the layered flavors.

Tools

Use the jigger to measure spirits precisely, the mixing glass and bar spoon to chill and dilute properly, and the strainer to keep ice shards out of the finished drink. The large ice cube slows dilution and keeps the drink balanced as it warms.