Cupcakes – 1 1/2 cups all-purpose flour sifted – 1/2 teaspoon baking powder – 1/4 teaspoon fine grain sea salt – 10 tablespoons unsalted butter at room temperature – 1 1/4 cups granulated sugar – 3 large eggs at room temperature – 1 1/2 teaspoons vanilla extract – 3 tablespoons whole milk at room temperature – 1/4 cup coconut rum or plain rum mixed with 1 teaspoon coconut extract

– 1/4 cup unsweet flake coconut or sweetened flake coconut chopped finer – 1/2 cup crushed pineapple drained

Coconut Buttercream – 1 cup unsalted butter at room temperature – 4 1/2 cups confectioners’ sugar – 1/4 teaspoon fine grain sea salt – 1/3 cup heavy whipping cream plus more to thin if needed – 2 1/2 teaspoons coconut extract – 1/3 cup toasted coconut for garnish (see notes) – 16 maraschino cherries drained and patted dry with paper towels

Cupcakes – Preheat the oven to 350F. Line cupcake pans with 16 cupcake liners. – Combine the flour, baking powder, and salt in a small bowl; whisk to combine. – In the bowl of an electric mixer, beat together the butter and sugar. Beat in eggs one at a time. Add the vanilla, milk, and rum, and mix on low speed. Beat for 3-5 minutes until the consistency is smooth. Add the flour mixture and beat until just combined.

– Add the flaked coconut and pineapple; fold in by hand. – Divide the batter between the prepared pans, filling each cavity about 2/3 full (a trigger ice cream scoop is perfect for portioning!). – Bake for 20-24 minutes, or until a toothpick tester comes out clean. Transfer cupcakes to a wire rack to cool completely.

Coconut buttercream – In the bowl of an electric mixer fitted with the whip attachment, beat together the butter and confectioners’ sugar on low speed.  When the mixture is just combined, add the salt and mix again. Increase the mixer speed to medium and add the heavy cream and coconut extract. When just combined, raise the speed to high and beat for 5-7 minutes. Add more heavy cream to reach smooth piping consistency, if needed. 

Beat until the frosting is lightened to almost white color and fluffy. – Transfer 1/2 of the frosting to a piping bag fitted with the 1/2-inch round tip. Transfer the other half to a piping bag fitted with the large closed star tip. – Place the toasted coconut on a shallow dish. – Pipe a circle of frosting around the top edge of a cupcake using the 1/2-inch round tip frosting bag. Immediately dip the edges of the frosting into the toasted coconut 

(see video for technique). – Pipe a swirl of frosting in the center of the cupcake using the large closed star tip frosting bag. Top with a maraschino cherry and a cocktail umbrella. – Repeat the process with the remaining cupcakes until they are all frosted and decorated.

Flake coconut: I use unsweet flake coconut for this recipe, which is finer and drier than sweetened flake coconut. You can use sweetened flake coconut instead. It tends to be damp and stringy, so chop it finer before adding it to this recipe. The end result will be slightly sweeter. To toast coconut, sprinkle it on a 13×9 baking sheet. Bake at 350F for 5-7 minutes or until golden brown. Cool before using on the cupcakes.

Whipped cream frosting alternative: To make these chilly for summertime, replace the coconut buttercream recipe with homemade whipped cream. Beat 1 1/2 cups heavy whipping cream in a stand mixer fitted with the whip attachment until soft peaks form.  Add 1/4 cup of fine granulated sugar while beating. Beat in 2 teaspoons coconut extract. Divide whipped cream between the designated piping bags with decorator tips and pipe as directed.

No alcohol version: Replace the 1/4 cup of rum with 1/4 cup canned coconut milk; add 1/2 teaspoon rum extract to the recipe.  You can also use 1/4 cup of pineapple juice in place of the rum. It may curdle the batter a little due to the pineapple enzymes, but will become more consistent when the flour mixture is added.