Caribbean Cocktails — The Painkiller & Piña Colada

The original Painkiller was created in the 1970s by Daphne Henderson at the Soggy Dollar Bar at White Bay on the island of Jost Van Dyke in the British Virgin Islands. The authenticity of this claim is asserted by Edward Hamilton’s The Complete Guide to Rum — as it points to the Soggy Dollar Bar in the ’70s. The Pain killer is considered by some as a glorified Piña Colada.

The differences between the recipes for the Painkiller and the Piña Colada may appear to be slight, but the flavor difference is tremendous.

A classic Piña Colada is made with pineapple juice, coconut cream, and light rum. It is blended in a blender with ice to create a slushy frozen drink or heavily shaken with ice. The Painkiller has the addition of orange juice and is served over ice, so as not to dilute, and is also topped with grated nutmeg. The orange juice adds a tangy sweetness which works beautifully with the coconut and the pineapple. 

The other major difference here of course, is the RUM.  The traditional recipe calls for Pusser’s Rum, but use what you prefer.  There are many different recipes, all using different proportions of rum. Apparently the folklore here is that depending on how bad your pain is what determines how much rum!

There are so many great recipes out there for a Pain Killer, and none taste as good as when you are toasting in the sunshine, so here is an alternative recipe for Pain Killer Popsicles. 

Edward Hamilton’s Complete Guide to Rum

Edward Hamilton’s Complete Guide to Rum

The Salty Dollar, Jost Van Dyke

The Salty Dollar, Jost Van Dyke




  •  8 ounces fresh pineapple peeled and cubed

  • 1 cup orange juice

  • 1/2 cup white rum divided

  • 1/3 cup plus 2 tablespoons unrefined cane sugar divided

  • 3 cups coconut milk

  • 1/2 cup toasted unsweetened flaked coconut

  • 4 oranges peel removed in one long strip with a vegetable peeler (avoiding the white pith)

  • 2 (3 inch) cinnamon sticks


  1. Process pineapple in a blender then push through a fine mesh seive so you remove most of the pulp (this should yield about 1 cup of pineapple juice). Combine pineapple mixture, orange juice, remaining 1/4 cup of the rum, and 1 to 2 tablespoons of the sugar (depening on how sweet you want the mixture). Fill each popsicle mold 1/3 full with the pineapple-orange mixture then put in the freezer until just frozen, at least 45 minutes. Meanwhile, make the coconut layer. 

  2. Whisk together coconut milk, remaining 1/3 cup of the sugar, 1/2 cup of the toasted coconut, orange peel, and cinnamon sticks in a saucepan and bring to a simmer over medium-high heat, about 5 minutes. Remove from heat, and set aside to cool at room temperature and to let the flavors steep, at least 30 minutes. Once the mixture is cool, remove the cinnamon stick, (grated nutmeg gets lost so cinnamon sticks are a great alternative) and orange zest, and add the remaining 1/4 cup of rum to the coconut milk mix.

  3. Once the pineapple-orange layer is frozen fill the popsicle molds the rest of the way with the coconut mixture (toasted coconut, coconut milk, and all). Garnish the top of the popsicle mold (which is actually the bottom of the popsicle once it's unmolded) with some more toasted coconut. Freeze until fully frozen, at least 3 1/2 hours.