1Core pineapple (leaving a few inches of fruit at the bottom to make an oversize vessel.) Freeze overnight in a Ziploc bag.
2o make demerara syrup: heat sugar with water over low in a small saucepan, stirring to dissolve. Let cool. Keep refrigerated.
3To make cocktail: Put a small amount of ice in a cocktail shaker, add bitters, demerara syrup, falernum, pear brandy, apricot liqueur, lemon juice, pineapple juice, and bourbon. Shake and strain into the cored and frozen pineapple. Add crushed ice, stir with a swizzle stick or long spoon. Add more crushed ice, garnish as desired.