In a large pitcher with ice, stir together the pineapple juice, bourbon, Simple Syrup and lime juice. Pour into ice-filled highball glasses, top with a splash of prosecco, garnish with a sprig of basil and serve.
Combine the sugar and 1 cup water in a small saucepan and bring to a boil. Cook, stirring, until the sugar dissolves. Remove from the heat and let cool completely. Keep covered in the refrigerator up to 1 month.