A nostalgic island-inspired classic showcasing golden pineapple rings caramelized in a glossy brown sugar glaze, resting atop a light, buttery vanilla sponge. Baked upside down and flipped to reveal its beautiful, sun-kissed topping, this retro favorite balances sweet, tangy fruit with tender cake in every slice. Perfect for potlucks, holiday tables, or whenever you crave a simple yet stunning homemade dessert that never goes out of style.
For the Topping:
1/2 cup (113 g) unsalted butter
1 cup (200 g) packed light brown sugar
7–8 pineapple rings (canned in juice, drained)
7–8 maraschino cherries
For the Cake:
1 1/2 cups (190 g) all-purpose flour
1 1/2 teaspoons baking powder
1/4 teaspoon salt
1/2 cup (113 g) unsalted butter, softened
3/4 cup (150 g) granulated sugar
2 large eggs
1 teaspoon vanilla extract
1/2 cup (120 ml) whole milk
1/4 cup (60 ml) reserved pineapple juice
Preheat oven to 350°F (175°C).
Melt 1/2 cup (113 g) butter in a 9-inch (23 cm) round cake pan and sprinkle 1 cup (200 g) brown sugar evenly over it.
Arrange pineapple rings and place cherries in the center of each ring.
In a bowl, whisk flour, baking powder, and salt.
Cream softened butter and granulated sugar until fluffy. Add eggs one at a time, then vanilla.
Alternate adding dry ingredients with milk and pineapple juice. Mix until just combined.
Spread batter over pineapple layer.
Bake 40–45 minutes or until a toothpick inserted in the center comes out clean.
Cool 10–15 minutes, then invert onto a serving plate.