Equipment Needed
- 10-inch cast-iron skillet or a 9-inch round cake pan
- Medium mixing bowl
- Large mixing bowl
- Handheld or stand mixer
- Whisk
- Spatula
- Small saucepan
- Cooling rack
- Large serving plate or platter
Step-by-Step Instructions
Let’s start where the magic happens: the skillet. I place my 10-inch cast-iron skillet on the stovetop and melt the 1/4 cup of butter over medium heat. Once it’s melted and foamy, I sprinkle the packed brown sugar evenly over the butter. I stir constantly for about 2-3 minutes until the sugar dissolves completely into the butter, creating a smooth, bubbling caramel. This is the foundation of your topping, so don’t rush it. I immediately remove the skillet from the heat. Now, I carefully arrange my drained pineapple rings in the caramel. I place a maraschino cherry in the center of each ring and fill any gaps with extra cherries or pineapple chunks. The pan is hot, so I use tongs! I then set the whole skillet aside to let the caramel cool and thicken slightly while I make the batter.
While the caramel sets, I preheat my oven to 350°F and make the cake batter. In my large bowl, I cream together the softened butter and granulated sugar until light and fluffy—this takes about 3 minutes with my mixer. I beat in the eggs, one at a time, followed by the vanilla extract. In a separate bowl, I whisk together the flour, baking powder, and salt. In a small measuring cup, I combine the milk and the reserved 1/3 cup of pineapple juice. The pineapple juice is the secret ingredient here; it adds a subtle, sweet-tart flavor that makes the cake taste distinctly tropical.
Now, with the mixer on low, I alternately add the dry ingredients and the milk/juice mixture to the butter mixture. I start and end with the dry ingredients, adding them in three parts and the liquid in two. I mix just until the batter is smooth and no dry streaks remain. It will be a thick, luxurious batter. Using a spatula, I carefully dollop the batter over the arranged pineapple and cherries in the skillet. I gently spread it into an even layer, being careful not to disturb my pretty fruit pattern. The smell at this point—sweet pineapple, vanilla, and caramel—is absolutely heavenly.(See the next page below to continue…)