Preheat your oven to 350°F (175°C).
Melt the butter in a 10-inch skillet over medium heat. Add the brown sugar and stir until dissolved. Remove from heat.
Arrange the pineapple slices on top of the brown sugar mixture. Place a cherry in the center of each pineapple slice.
In a mixing bowl, whisk together the flour, granulated sugar, baking powder, and salt.
In another bowl, combine the milk, pineapple juice, vanilla extract, and eggs. Mix well.
Gradually add the wet ingredients to the dry ingredients, mixing until just combined.
Pour the batter over the pineapple slices in the skillet.
Bake in the preheated oven for 30-35 minutes, or until a toothpick inserted into the center comes out clean.
Let the cake cool in the skillet for 10 minutes, then invert onto a serving plate.