Step 1

Make vanilla bean simple syrup: in a small sauce pan combine 1 cup water, 1 cup granulated sugar and one fresh vanilla bean cut in half lengthwise and scraped. Make sure to scrape all of the vanilla bean seeds into the pot. Whisk to combine and bring to a simmer over medium heat. Once the sugar is completely dissolved, remove from heat and transfer allow to steep until cooled. Transfer to a mason jar and keep in the refrigerator until ready to use. (keep the vanilla bean in the syrup to further infuse.)

Step 2

In a cocktail mixing glass filled with large ice cubes, add bourbon, vanilla bean syrup, and bitters.

Step 3

Stir well to chill and dilute the bourbon.

Step 4

Strain drink into a cocktail glass with one large ice cube.

Step 5

Crush a slice of orange peel over the glass to express the oils and add to the drink for garnish.

Step 6

Add a Luxardo cherry and vanilla bean for garnish.