Pineapple rings and maraschino cherries are arranged in the bottom of a buttered, brown-sugar-coated pan before the batter goes in, so the fruit caramelizes as the cake bakes and becomes the top when it's flipped. The result is a moist, buttery cake with a glossy, caramelized fruit layer. It comes together in about an hour.
Preheat the oven to 180°C (350°F). Grease a 9-inch (23cm) round cake pan.
Pour the melted butter into the prepared pan, then sprinkle evenly with the brown sugar. Arrange the pineapple slices and cherries in a decorative pattern atop the brown sugar layer.
Whisk together the flour, baking powder, and salt in a medium bowl. Set aside.
In a large bowl, beat the softened butter with the granulated sugar on high speed until creamy, about 2 minutes. Add eggs and vanilla, mixing until combined.
Alternately add the dry ingredients and the combined pineapple juice and milk, starting and ending with the dry ingredients. Mix on low speed until just combined; do not overmix.
Pour the batter evenly over the pineapple layer, smoothing it with a spatula.
Bake for 40–45 minutes, or until a toothpick inserted into the center of the cake comes out clean.
Allow the cake to cool in the pan for 10 minutes, then carefully invert onto a serving plate. Cool for at least 30 minutes before serving warm or at room temperature.
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Notes
Tips: For a more robust flavor, try adding a teaspoon of dark rum to the mix. Substitute coconut milk for a tropical twist. Ensure all ingredients are at room temperature for the best texture.