Preheat the oven to 350°F (175°C) and line a cupcake tin with paper liners.
In a large bowl, cream the softened butter and granulated sugar until light and fluffy.
Add the eggs one at a time, mixing well after each addition, then stir in the vanilla extract.
In another bowl, combine the flour, baking powder, and salt.
Alternate adding the dry ingredients and the buttermilk to the butter mixture, starting and ending with the dry ingredients.
Fold in the crushed pineapple gently until just combined.
Divide the batter evenly into the prepared cupcake tins, filling each liner about two-thirds full.
Bake for 18-20 minutes, or until a toothpick comes out clean when inserted in the center.
Allow the cupcakes to cool in the pan for 5 minutes, then transfer to a wire rack to cool completely.
While the cupcakes cool, prepare the frosting by whipping the heavy cream until soft peaks form, then slowly add the powdered sugar and coconut extract.
Once the cupcakes are completely cool, frost them generously with the whipped cream mixture.
Garnish each cupcake with a maraschino cherry on top before serving.