Bourbon Pineapple Upside Down Cake Recipe
Introduction
This Bourbon Pineapple Upside Down Cake is a delightful twist on a classic dessert, combining caramelized pineapple rings with a moist, flavorful cake. The addition of bourbon adds depth and warmth, making it perfect for any occasion where you want to impress with a homemade treat.

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: In a small saucepan over medium heat, melt the butter. 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. The mixture will bubble briefly. Gently add the pineapple slices to the saucepan and coat them in the sauce with a spoon. Set aside while preparing the cake batter.
- Step 4: In a medium bowl, whisk together the flour, granulated sugar, baking soda, baking powder, salt, and cinnamon. In a large bowl, combine the eggs, oil, sour cream, vanilla extract, and reserved pineapple juice. Whisk the wet ingredients until fully combined.
- Step 5: Pour the dry ingredients into the wet ingredients and gently fold with a rubber spatula until just combined. Avoid overmixing.
- Step 6: To assemble, pour a thin layer of the bourbon brown sugar sauce into the prepared cake pan, coating the bottom evenly. Arrange the pineapple slices over the sauce, overlapping or cutting to fit if needed. Pour the remaining sauce over the pineapples.
- Step 7: Carefully spoon the cake batter over the pineapple and sauce, spreading evenly with an offset spatula or spoon.
- Step 8: Bake for about 45 minutes, or until a toothpick inserted in the center comes out clean. Let the cake rest in the pan for at least 10 minutes before carefully inverting onto a plate. Serve warm and enjoy!
Tips & Variations
- Use fresh pineapple slices for a brighter flavor, but reduce added pineapple juice slightly.
- For a non-alcoholic version, replace bourbon with pineapple juice or apple cider.
- Add chopped pecans or walnuts to the topping for extra texture and flavor.
- Make mini cakes using individual ramekins for a fun presentation.
Storage
Store leftover cake covered tightly at room temperature for up to 2 days. For longer storage, refrigerate in an airtight container for up to 5 days. Warm slices gently in the microwave or oven before serving to bring back moistness and aroma.
How to Serve

Serve this delicious recipe with your favorite sides.
FAQs
Can I use fresh pineapple instead of canned?
Yes, fresh pineapple works well but contains less juice, so reduce the added pineapple juice in the recipe slightly to maintain the right cake texture.
What can I substitute for bourbon?
If you prefer no alcohol, substitute the bourbon with an equal amount of pineapple juice or apple cider for a similar depth without the alcohol flavor.
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Bourbon Pineapple Upside Down Cake Recipe
- Total Time: 1 hour 5 minutes
- Yield: 8–10 servings 1x
Description
This Bourbon Pineapple Upside Down Cake is a decadent twist on a classic dessert, featuring caramelized pineapple rings infused with a rich bourbon brown sugar glaze. Moist and tender cake layers are flavored with vanilla and pineapple juice, making a perfect balance of sweet, boozy, and tropical notes. Ideal for an indulgent treat or special occasion.
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 (reserved from canned pineapple slices)
- 3 tablespoons bourbon
- 20 ounce 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 to prevent sticking, then set it aside.
- Make the bourbon brown sugar topping: In a small saucepan over medium heat, melt the butter. Once fully melted, whisk in the brown sugar until combined. Add vanilla bean paste or extract and 4 tablespoons of the reserved pineapple juice. Let this mixture simmer gently for about 2 minutes, stirring occasionally.
- Add bourbon and pineapple slices: Turn off the heat and carefully pour in the bourbon while stirring. The mixture will bubble briefly due to the alcohol. Then add the pineapple slices to the saucepan, coating each ring thoroughly in the sauce. Let this mixture rest 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 until fully combined. In a separate large bowl, whisk together the eggs, oil, sour cream, vanilla extract, and 1/4 cup pineapple juice until smooth. Gently fold the dry ingredients into the wet 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 cake pan to coat it evenly. Arrange the pineapple slices over the sauce; overlap or cut slices as needed to fit them all in a single layer. Pour the remaining sauce evenly over the pineapple rings. Carefully pour the cake batter on top and spread evenly using an offset spatula or spoon.
- Bake and serve: Bake the cake in the preheated oven for about 45 minutes, or until a toothpick inserted into the center comes out clean. Allow the cake to cool in the pan for at least 10 minutes, then invert it onto a large plate or cake stand, being mindful as juices may run. Slice and serve warm for best flavor and texture. Enjoy!
Notes
- Use full-fat sour cream for a moist and rich cake texture.
- The bourbon adds warmth and flavor but can be omitted or substituted with vanilla extract for a non-alcoholic version.
- For even better flavor, you can toast the pineapple slices lightly before adding them to the sauce.
- Letting the cake sit a little before inverting makes it easier to release from the pan.
- Serve warm with a scoop of vanilla ice cream for an extra special dessert.
- Prep Time: 20 minutes
- Cook Time: 45 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Keywords: Bourbon Pineapple Upside Down Cake, pineapple cake, upside down cake, bourbon dessert, caramelized pineapple cake, moist cake, easy cake recipe

