Split the vanilla bean lengthwise and scrape seeds into a small saucepan. Add the scraped pod (or 1 tsp pure vanilla extract later), sugar, and water. Bring to a gentle simmer over medium heat, stirring until sugar dissolves. Remove from heat and let steep 30 minutes (longer for stronger flavor). If using extract, stir it in after cooling. Strain out the pod and cool. Store refrigerated up to 2 weeks.

Build the Cocktail

Add ingredients to mixing glass

In a mixing glass or cocktail shaker, add 2 oz Sagamore Rye, 0.25 oz allspice dram, 0.25 oz vanilla syrup, and 2 dashes orange bitters.

Add ice and dilute

Fill the mixing glass with plenty of ice and stir gently for 20–30 seconds until well chilled and slightly diluted (aim for about 20–25% dilution by eye — the spirit should be cold and slightly melted).

Prepare glass and strain

Place a large ice cube in an Old Fashioned or rocks glass. Optionally rinse the glass with 0.25 oz cold water (or a small rinse of rye) to soften the edges. Strain the chilled cocktail over the large ice cube.

Express and garnish

Take an orange peel and express the oils over the drink by holding the peel skin-side down about 2–3 inches over the glass and giving it a firm twist. Rub the peel around the glass rim and drop it into the drink. Add a Luxardo or brandied cherry on a pick.

Serve

Serve immediately. Sip slowly to enjoy the interplay of rye spice, the warm allspice note, and the vanilla sweetness balanced by orange bitters.