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bourbon pineapple upside down cake on white dish

Bourbon Pineapple Upside Down Cake

  • Author: Quin Liburd
  • Prep Time: 5m
  • Cook Time: 50m
  • Total Time: 55m
  • Yield: 6 1x
  • Category: Desserts and Sweets
  • Method: Baking
  • Cuisine: American


This bourbon pineapple upside down cake is so good! The cake is moist, flavorful, and wonderfully spiced- topped with a killer and dreamy bourbon brown sugar glaze that soaks into the cake!



Bourbon Brown Sugar Topping

  • 1/2 cup (1 stick) unsalted butter
  • 3/4 cup light brown sugar
  • 1 teaspoon vanilla bean paste, or vanilla extract
  • 20 ounce canned pineapple slices in pineapple juice, juice divided
  • 3 tablespoons Evan Williams Honey Bourbon

For The Cake

  • 1 1/2 cups all-purpose flour
  • 1/2 cup white granulated sugar
  • 2 teaspoons baking soda
  • 1 teaspoon baking powder
  • 1 teaspoon kosher salt
  • 1/2 teaspoon ground cinnamon
  • 2 large eggs
  • 1 cup vegetable oil, or canola oil
  • 8 ounces full-fat sour cream
  • 2 teaspoons vanilla extract
  • 1/4 cup pineapple juice, from reserved can of pineapple slices


  1. Preheat the oven to 350°F. Generously butter/spray a 10-inch round cake pan and set aside.
  2. For the bourbon brown sugar topping: In a small saucepan over medium heat, melt the butter. Once the butter has melted down, add in the brown sugar and whisk together with the butter. Add in the vanilla bean paste/extract and four tablespoons of the pineapple juice. Let the mixture come up to a nice simmer, about 2 minutes, while stirring every so often. 
  3. Turn off the heat and carefully pour in the bourbon and stir together to fully incorporate. The mixture will bubble vigorously for a quick second due to the alcohol. Then gently add in the pineapple slices in the same saucepan and use a spoon to coat each pineapple ring in the sauce. Let the saucepan hang so the mixture can sit together while you prepare the cake.
  4. For the cake: In a medium bowl, combine the flour, granulated sugar, baking soda, baking powder, salt, and cinnamon. Give everything a good whisk to fully combine. In another large bowl- combine the eggs, oil, sour cream, vanilla extract, and pineapple juice. Whisk the wet ingredients together to fully incorporate. Pour the dry ingredients into the wet ingredients bowl and use a rubber spatula to gently fold everything together until just combined. 
  5. To assemble cake: In the 10-inch round cake pan, take the saucepan and pour in a little of the sauce (just enough to fully coat the entire bottom of the pan). Then take each pineapple ring and place them all around the bottom of the pan. You may not be able to place each one in a single layer so feel free to overlap them or cut into pieces to fit all around. Then pour the remaining sauce evenly all over the tops of the pineapple rings. Carefully empty the cake batter on top and use an offset spatula/spoon to spread it evenly over the sauce/pineapple rings.
  6. Bake the cake for 45 minutes or until a toothpick inserted into the center of cake comes out clean. Allow the cake to sit in the pan for at least 10 minutes and then carefully invert the cake onto a large cake stand or plate as juices will run. Cut into slices and serve warm. Enjoy!


  1. You will need a 20 ounce can of pineapple slices in juice, about 10 pineapple rings. Alternatively, you can also use a fresh whole pineapple that is cut and cored.
  2. This cake will keep stored in an airtight container for up to three days when stored in the fridge and up to one month when stored in the freezer.
  3. Please read the blog post in its entirety for more tips + tricks.

Keywords: pineapple, cake, dessert, bourbon, sweets