Chill an Old Fashioned (rocks) glass by filling it with ice and set aside. In a mixing glass, add 2 oz High West Rendezvous bourbon (or your chosen high-rye bourbon), 0.5 oz rye whiskey if you want a spicier profile (optional but included in ingredient list), 0.5 oz amaro, 0.5 oz sweet vermouth, 0.25 oz tawny port, 0.25 oz cherry liqueur, 2 dashes Angostura bitters, and 1 dash orange bitters.

Add ice and stir

Fill the mixing glass about three-quarters full with large ice cubes. Stir gently but thoroughly for 30–45 seconds (or about 20–30 full rotations) until the mixture is well chilled and properly diluted (the mixing glass will fog and the liquid will slightly clear).

Prepare serving glass

Discard the ice from the chilled Old Fashioned glass and, if desired, place a single large ice cube or sphere into the glass.

Strain

Using a julep or Hawthorne strainer, strain the stirred cocktail from the mixing glass into the prepared rocks glass over the large ice cube.

Garnish & Finish

Zest and rim

Express the orange peel over the drink: hold the peel skin-side down about 3–4 inches above the surface and give it a sharp twist to spray the oils over the cocktail. Run the peel around the rim of the glass for extra aromatic lift, then drop it into the drink or rest it on the edge.

Cherry garnish

Skewer or drop a Luxardo or brandied cherry into the glass as a finishing touch. Serve immediately.