Grilled Pineapple Upside-Down Skillet Cake

Grilled Pineapple Upside-Down Skillet Cake

As a kid I did not have the sweet tooth my brother and sister had. I always preferred a salty or spicy treat versus a sweet dessert. The only thing that distracted my savory tooth was when my mom baked homemade cakes. My mom used to make a warm classic pineapple upside-down cake made with yellow cake mix that was simply sinful. This recipe is inspired by mom’s cake, but made from scratch and is baked in a cast-iron skillet and topped with fresh grilled pineapples.

Watch my video and learn how to cut a pineapple like a pro.

grilled pineapple

The cake is not grilled, but the fresh pineapple slices are. Grilled pineapple gives them a candied caramel flavor. The key is not to char the pineapple, but to just achieve golden brown delicious coloring on your fruit.

buttery brown sugar pineapples

Who can resist gooey pineapple and cherries coated with a buttery brown sugar glaze? This cake is super-moist, full of flavor, light, and tender.

Pineapple Upside-Down Cake

Grilled Pineapple Upside-Down Skillet Cake


  • Fresh pineapple slices
  • 1 tablespoon vegetable oil
  • 11 tablespoons unsalted butter, divided
  • ¾ cup packed light brown sugar
  • 1⁄3 cup maraschino cherries without stems
  • 1½ cups all-purpose flour
  • 1½ teaspoons baking powder
  • ¼ teaspoon salt
  • ¾ cup granulated sugar
  • 1 teaspoon pure vanilla extract
  • 2 eggs
  • ½ cup milk


  1. Lightly brush both sides of pineapple rings with vegetable oil and grill them, turning once, until lightly charred, about 3 minutes per side. Let cool and set aside.
  2. Melt 3 tablespoons of butter in a 10-inch cast-iron skillet. Add brown sugar and cook while stirring, until sugar is melted and begins to bubble. Remove from heat and cool. Once cool, arrange the pineapple slices in the melted sugar and add cherries pineapple slices. Set aside.
  3. Preheat oven to 350 degrees F.
  4. In a bowl sift the flour, baking powder, and salt.
  5. In a separate bowl, beat remaining 8 tablespoons butter and the granulated sugar until creamy. Add the vanilla and then the eggs, one at a time, beating until smooth.
  6. Add the flour mixture little by little as you slowly stir in the milk. Do not over mix: stir just until the flour is incorporated into the batter.
  7. Pour cake batter over fruit in skillet, using a spoon to gently spread it to the edge.
  8. Bake for 30 to 40 minutes, until a toothpick inserted in the middle comes out clean.
  9. Remove from oven. Let cool about 5 to 10 minutes—do not let cool too long or it will stick in your skillet. Place a cake platter over skillet and, wearing oven mitts, carefully flip the cake onto the cake platter.

I’d love to see what you cook!

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