How to Make It
In a cocktail shaker, combine the bourbon, Pineapple Vinegar, lemon juice and Simple Syrup. Fill the shaker with ice, shake well and strain into a chilled, ice-filled highball glass. Float the Madeira on top, slowly pouring it over the back of a bar spoon near the drink’s surface.
Pineapple Vinegar: In a medium saucepan, simmer 4 ounces unsweetened pineapple juice over high heat until reduced by half, about 7 minutes. Remove from the heat and stir in 6 ounces white vinegar and 1/4 cup sugar. Let stand until the sugar completely dissolves, about 10 minutes. Pour the infused vinegar into a jar and refrigerate for up to 3 weeks. Makes about 9 ounces.