Using the cherry pitter, remove the pits from each of the cherries. It’s important to keep the cherries as whole as possible, so that they can be used as beautiful garnishes later. Be warned – this part can get messy!
In a heavy bottomed, non-reactive sauce pan, combine the water and sugar and bring to a low boil. Add the vanilla bean and stir until the sugar is completely dissolved. Remove from heat and stir in the lemon juice.
Pack the cherries into the half pint jars until they are three-fourths full. Ladle the simple syrup into each jar to the same three-fourths height. Then, top each jar with about ¼-ounce orange liqueur and 1-ounce bourbon, leaving a ½ inch of head space. You may need to add a little more syrup or a little more liqueur to meet that level, as needed.
Wipe the rims clean, apply the lids and screw on the bands to finger tip tightness. Process the jars in a hot water bath for 15 minutes, then remove the canning pot from heat and allow the jars to vent in the pot for an additional 10 minutes (This will prevent potential leaking when the jars are removed). Let the jars rest for 24 hours. If any do not seal, store in the fridge.
Store sealed jars in a cool dark space, letting the cocktail cherries cure in the sugar-liqueur mixture for at least 2 weeks before using. Once opened, store jars in the fridge and use within 3-4 weeks.