Add the strawberry syrup and bitters to mixing glass and stir to combine.
Fill the mixing glass with ice then pour in bourbon and stir until chilled to the touch (about eight seconds).
Strain the liquid into a rocks glass over a large ice cube.
Peel off a strip of orange rind then squeeze it over top of the cocktail to express oils and drop peel into the glass for garnish.
Notes
Making the Strawberry Vanilla Syrup
Hull and slice eight ounces of strawberries and split open one vanilla bean to expose its seeds.
Add strawberries and vanilla bean to a small saucepan with one cup of water and one cup of sugar (or other sweetener) over medium heat.
Stir to dissolve the sugar and bring the mixture to a boil then reduce heat to low and simmer for 10 minutes.
Remove from heat and strain out solid ingredients then allow syrup to cool fully before using. Makes 10 servings.
PreparationYou can mix this drink up to two days in advance and store in the refrigerator or freezer. Reserve the ice until serving and stir up the cocktail in case of separation.To batch this drink, combine two ounces of strawberry vanilla syrup and 8-12 dashes of bitters. Add ice then six ounces of bourbon and stir until chilled. Divide the liquid between four rocks glasses over fresh ice then express orange oil over each one. Serves four but if you need more just adjust the servings in the recipe card below!Cocktail Tool SubstitutionsInstead of a cocktail mixing glass and a bar spoon you could use a highball glass and a regular table spoon or butter knife.If you don't have a jigger to measure the liquor, use a standard size shot glass as it holds roughly the same amount of liquid as the larger end of the jigger.If you don't have a cocktail strainer you can use another glass to cover all but a sliver of the mixing glass as you pour so that just the liquid comes out. A mesh strainer will also work.