Pineapple Upside Down Cake with Pineapple Balsamic

by Alex Cogen
Pineapple Upside Down Cake with Pineapple Balsamic - Texas Hill Country Olive Co.

Pineapple upside down cake is one of those classic cake recipes that we go back to time and time again. And this recipe stands out from the rest with our use of Pineapple Balsamic Vinegar!

Using balsamic in this recipe adds a delightful twist to the traditional pineapple upside-down cake. Pineapple Balsamic Vinegar is crafted by infusing high-quality balsamic vinegar with the sweet, tangy essence of ripe pineapples. Using equal parts pineapple juice and balsamic in the pineapple cake base, you guarantee extra flavor that is the perfect balance of sweet and tart.

One necessary ingredient when making a good cake? Extra Virgin Olive Oil! Using olive oil instead of butter not only imparts a delicate complexity and moistness to the cake, but it adds a dose of healthy ingredients and lessens the use of unhealthy butter. Plus, our Sola Stella Extra Virgin Olive Oil still yields a buttery cake with it's delicate flavor profile!

Pineapple Upside Down Cake with Pineapple Balsamic


For the topping:

  • 1/4 cup butter, unsalted
  • 1/2 cup of brown sugar
  • 1 fresh pineapple, peeled, cored, and cut into rings
  • Maraschino cherries, drained (optional)

For the cake batter:

Pineapple Upside Down Cake


  1. Preheat your oven to 350°F (175°C). Grease a 9-inch round cake pan and line the bottom with parchment paper for easier removal.

  2. In a small saucepan, melt the unsalted butter over low heat. Once melted, add the brown sugar to the melted butter and stir until it dissolves completely. Pour this mixture into the prepared cake pan, spreading it evenly.

  3. Arrange the fresh pineapple slices over the brown sugar mixture in the pan. You can also place a maraschino cherry in the center of each pineapple ring, if desired.

  4. In a medium mixing bowl, sift together the cake flour, baking powder, baking soda, and salt. Set aside.

  5. In a separate large bowl, whisk together the olive oil and granulated sugar until well combined. Add the eggs, one at a time, beating well after each addition. Stir in the vanilla extract.

  6. Gradually add the dry ingredients to the wet ingredients, alternating with the pineapple juice and pineapple balsamic vinegar, mixing until just combined. Be careful not to overmix.

  7. Pour batter over the pineapple rings in the regular cake pan, spreading it evenly to cover them.

  8. Bake in the preheated oven for 35-40 minutes, or until a toothpick inserted into the center of the cake comes out clean.

  9. Remove the cake from the oven and let it cool in the pan for 10 minutes. Then, carefully invert the cake onto a serving plate. Be cautious, as the pan and caramelized sugar will be hot.

  10. Let the cake cool completely to room temperature before serving. Add powdered sugar to the top of the cake, if desired.

Time to Enjoy!

This is the best pineapple upside-down cake around - and we can't wait for you to try it! This retro cake is one of those classic recipes that never disappoints. Place it on a serving platter on special occasions, like a summer feast or Easter brunch. 

By opting for extra virgin olive oil instead of vegetable oil or butter, you will create an olive oil cake that is a little less guilt-free (it is still a cake, after all).

Looking for more cake recipes featuring olive oil and balsamic vinegar? Check out some of our favorites:

Click below for a downloadable version of this easy pineapple upside-down cake recipe card!

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