Toss the simple syrup, Ritrovo Selection Organic Amarena Cherry Balsamic, mint leaves, lemon slices, and cherries into a cocktail shaker. Muddle with a cocktail muddler or handle of wooden spoon until the lemons break down and the mint releases its oil.
Add the bourbon and fill the shaker with ice. Place the top on the cocktail shaker and vigorously shake until well chilled, about 15 seconds.
Pour into a chilled martini glass and top with a splash of club soda, garnish with a lemon slice, big mint sprig, and a fresh cherry or two.