Add all the ingredients into a shaker with ice and shake until well-chilled.
Strain into a hurricane glass over pebble ice.
Garnish with an Angostura bitters float.
*Grilled pineapple purée: Remove the skin and top from a ripe pineapple and cut into 1/3-inch slices. Grill until caramelized. Add caramelized pineapple slices to a Vitamix or powerful blender, and purée until smooth.