Preheat the oven to 350°F (175°C) and line a cupcake pan with liners.
In a mixing bowl, cream the butter and sugars until light and fluffy.
Add eggs one at a time, mixing well after each addition.
Stir in the vanilla extract and milk until combined.
In another bowl, whisk together flour, baking powder, and salt.
Gradually add the dry ingredients to the wet mixture, mixing until just combined.
Place a pineapple ring at the bottom of each cupcake liner, adding a cherry in the center.
Spoon the batter evenly over the pineapple and cherry.
Bake for 20-25 minutes, or until a toothpick comes out clean.
Allow to cool for 10 minutes, then invert onto a wire rack to cool completely.