Cherry Tomato Balsamic Shrub: Combine chopped tomatoes and sugar in a bowl and mix well. Cover and allow tomatoes to macerate for 4–8 hours. Add balsamic vinegar, blend until smooth, and strain through a fine mesh strainer. Store in the refrigerator for up to 6 months.
Strawberry Syrup: Combine strawberries and sugar in a bowl and mix to coat evenly. Allow strawberries to macerate for 4–8 hours. Add water and blend until smooth. Double strain through a fine mesh strainer and store in the refrigerator for up to 3 months.
To prepare a cocktail, add bourbon, shrub, syrup, aperitif, and basil leaves to an ice-filled shaker. Shake then strain into a chilled coupe glass. Finish with bitters and garnish with a skewer of cherry tomato, strawberry, and basil.