Bourbon Pineapple Upside Down Cake Recipe
Introduction
This Bourbon Pineapple Upside Down Cake is a delightful twist on a classic dessert, combining caramelized pineapple with a hint of warm bourbon. Moist and flavorful, it’s perfect for any occasion where you want to impress with minimal effort.

Ingredients
- 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 bourbon
- 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
Instructions
- Step 1: Preheat the oven to 350°F. Generously butter or spray a 10-inch round cake pan and set aside.
- Step 2: For the bourbon brown sugar topping, melt the butter in a small saucepan over medium heat. Once melted, add the brown sugar and whisk together. Stir in the vanilla bean paste or extract and four tablespoons of pineapple juice. Let the mixture simmer for about 2 minutes, stirring occasionally.
- Step 3: Turn off the heat and carefully pour in the bourbon, stirring to combine. It will bubble vigorously briefly. Gently add the pineapple slices to the saucepan and spoon the sauce to coat each ring. Let sit while you prepare the cake batter.
- Step 4: In a medium bowl, whisk together the flour, granulated sugar, baking soda, baking powder, salt, and cinnamon until combined. In a separate large bowl, whisk the eggs, oil, sour cream, vanilla extract, and 1/4 cup reserved pineapple juice until smooth.
- Step 5: Pour the dry ingredients into the wet ingredients bowl and gently fold with a rubber spatula until just combined. Do not overmix.
- Step 6: Pour a small amount of the bourbon brown sugar sauce into the prepared cake pan, spreading it evenly to coat the bottom. Arrange the pineapple slices over the sauce, overlapping or cutting pieces to fit if necessary. Pour the remaining sauce over the top of the pineapple rings.
- Step 7: Carefully pour the cake batter over the pineapple and sauce, spreading evenly with a spatula.
- Step 8: Bake for 45 minutes or until a toothpick inserted into the center comes out clean. Let the cake rest in the pan for at least 10 minutes, then invert onto a large plate or cake stand. Serve warm and enjoy!
Tips & Variations
- Use fresh pineapple rings for a brighter flavor, but reduce added pineapple juice accordingly.
- For a non-alcoholic version, substitute bourbon with pineapple juice or apple cider.
- To enhance the aroma, toast the brown sugar mixture gently and avoid burning the butter.
- Serve with a scoop of vanilla ice cream or a dollop of whipped cream for extra indulgence.
Storage
Store the cake tightly covered at room temperature for up to 2 days or refrigerated for up to 4 days. Reheat slices gently in the microwave or oven before serving to enjoy the warm, melty topping.
How to Serve
Serve this delicious recipe with your favorite sides.
FAQs
Can I use fresh pineapple instead of canned?
Yes, fresh pineapple rings work well, but be sure to reduce the additional pineapple juice in the recipe to avoid excess moisture.
Is it necessary to use bourbon in the recipe?
No, bourbon adds a unique flavor, but you can substitute it with additional pineapple juice or a non-alcoholic extract if preferred.
PrintBourbon Pineapple Upside Down Cake Recipe
This Bourbon Pineapple Upside Down Cake is a luscious twist on a classic dessert, featuring caramelized pineapple rings infused with a rich bourbon brown sugar sauce and a moist, tender cake layered on top. Perfectly balanced with warm spices and a hint of vanilla, this cake is baked to golden perfection and served warm for a delightful treat.
- Prep Time: 20 minutes
- Cook Time: 45 minutes
- Total Time: 1 hour 5 minutes
- Yield: 10 servings 1x
- Category: Dessert
- Method: Baking
- Cuisine: American
Ingredients
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
- 4 tablespoons pineapple juice (from canned pineapple slices)
- 3 tablespoons bourbon
- 20 ounces canned pineapple slices in pineapple juice, juice reserved
Cake Batter
- 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 pineapple juice)
Instructions
- Preheat and Prepare Pan: Preheat your oven to 350°F (175°C). Generously butter or spray a 10-inch round cake pan and set it aside to prepare for the topping.
- Make Bourbon Brown Sugar Topping: In a small saucepan over medium heat, melt the butter. Once fully melted, whisk in the brown sugar until well combined. Stir in the vanilla bean paste or extract and 4 tablespoons of the pineapple juice. Allow the mixture to simmer gently for about 2 minutes, stirring occasionally.
- Add Bourbon and Pineapple: Turn off the heat and carefully pour in the bourbon, stirring to incorporate fully. The mixture will bubble vigorously due to the alcohol. Add the pineapple slices to the saucepan, coating each ring with the sauce using a spoon. Let the mixture sit while you prepare the cake batter.
- Prepare the Cake Batter: In a medium bowl, whisk together the flour, granulated sugar, baking soda, baking powder, salt, and cinnamon. In a separate large bowl, combine the eggs, oil, sour cream, vanilla extract, and 1/4 cup pineapple juice. Whisk the wet ingredients until smooth, then gently fold in the dry ingredients with a rubber spatula until just combined. Avoid overmixing.
- Assemble the Cake: Pour a thin layer of the bourbon-brown sugar sauce into the bottom of the prepared 10-inch cake pan. Arrange the pineapple slices over the sauce, overlapping or cutting rings if necessary to fit them all. Pour the remaining sauce evenly over the pineapple slices. Carefully pour the cake batter on top, spreading it evenly with an offset spatula or spoon.
- Bake and Serve: Bake the cake for 45 minutes, or until a toothpick inserted into the center comes out clean. Let the cake rest in the pan for at least 10 minutes before carefully inverting it onto a large cake stand or serving plate. Serve warm, slicing to enjoy the caramelized bourbon pineapple topping.
Notes
- Use full-fat sour cream for best texture and moistness in the cake.
- Be cautious when adding bourbon to the hot mixture as it will bubble vigorously due to the alcohol content.
- If you prefer a non-alcoholic version, substitute bourbon with additional pineapple juice or apple juice.
- Allow the cake to cool slightly before inverting to avoid breaking the edges.
- The cake is best enjoyed warm but can be served at room temperature.
Keywords: Bourbon Pineapple Upside Down Cake, bourbon cake, pineapple dessert, caramelized pineapple cake, baked cake recipe, classic upside down cake

