Pineapple simply screams summer. Whether it’s cut into spears or wedges for easy snacking or blended in a piña colada for a weekend happy hour, pineapple’s tropical flavor begs to be enjoyed when the sun is out. Let’s take another step toward pineapple bliss with this twist on a pineapple upside down cake.

A mélange of melted butter and brown sugar creates a delicious caramel base for the pineapple before it’s covered with vanilla cake batter and baked, to perfection, of course. Traditionally, a pineapple upside cake includes maraschino cherries nestled in between the pineapple slices before baking, but this recipe uses fresh Harry & David cherries that are added right before serving for a fruity punch. The magic comes at the end when the cake is flipped upside down (hence the cake’s name!) and the decadent pineapple slices are revealed and topped with fresh cherries. 

This cake really couldn’t be easier to make!

Pineapple Upside Down Cake

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Prep Time 40 minutes
Cook Time 45 minutes
Resting time 15 minutes
Total Time 1 hour 40 minutes
Servings 8


  • 1 10 inch deep dish cake pan


  • 5 tablespoons melted butter
  • ½ cup and ¾ cup light brown sugar (separated)
  • 6-8 slices pineapple
  • 1 ⅓ cups all-purpose flour
  • 2 teaspoons baking powder
  • ½ teaspoon salt
  • ¼ cup butter
  • ¾ cup milk
  • 1 teaspoon vanilla
  • 1 egg
  • 3 tablespoons pineapple juice

For serving


  • Preheat oven to 350˚ F.
  • Pour melted butter into the bottom of a 10-inch deep-dish cake pan and sprinkle 1/2 cup brown sugar evenly over top.
  • Arrange the pineapple slices on top of the butter mixture and up the sides, if desired. Set aside.
  • In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.
  • In a large bowl, beat the remaining brown sugar and butter together until smooth. While stirring, slowly add the milk, vanilla, egg, and pineapple juice until combined.
  • Add the dry ingredients to the wet mixture and beat until combined with no lumps.
  • Pour the batter over the pineapple and spread evenly — some of the fruit may poke through the batter.
  • Bake for 45 minutes or until golden brown and the top springs back when pressed with your finger.
  • Allow the cake to cool in the pan for 5 minutes then flip it onto a plate or platter and leave the pan on the cake for 10 minutes longer.
  • Carefully remove the cake pan and allow the cake to cool to room temperature.
  • Top with cherries and whipped cream before serving.
Course: Dessert
Cuisine: American
Keyword: cake, cherries, pineapple
Tried this recipe? Snap a pic and share.Mention @harryanddavid or tag #sharemore!

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Autumn Micketti is the SEO & Content Coordinator for 1-800-Flowers. When she's not writing about Oregold® Peaches or love songs, you can find her exploring mountains, listening to the latest album release of her current musical obsession, or spending time with her extended family.

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