This Pineapple Upside Down Cake is a nostalgic treat that combines caramelized pineapple with a moist, buttery cake for a dessert that’s as beautiful as it is delicious. The golden pineapple rings, glazed with a sticky brown sugar topping, create a luscious, sweet base that’s perfectly balanced by the tender crumb of the cake. Ready in just over an hour, it’s a showstopper that’s surprisingly simple to make.
Every bite offers a harmony of textures, from the juicy pineapple to the soft, fluffy cake, with a hint of vanilla warmth tying it all together. Whether served warm or at room temperature, this cake is a crowd-pleaser that brings a touch of tropical sunshine to any occasion. Perfect for sharing, it’s a dessert that feels both indulgent and comforting.
Ingredients for Pineapple Upside Down Cake
- Topping:
- ¼ cup (60 g) salted butter, melted
- ½ cup (100 g) brown sugar, tightly packed (light or dark, light preferred)
- 10 pineapple slices, patted dry (a 20oz can typically provides enough)
- Maraschino cherries, as needed
- Vanilla Cake:
- ½ cup (115 g) unsalted butter, softened to room temperature
- ¾ cup (150 g) granulated sugar
- 2 large eggs, room temperature preferred
- 1 teaspoon vanilla extract
- 1 ½ cups (195 g) all-purpose flour
- 1 ½ teaspoons baking powder
- ¼ teaspoon salt
- ½ cup (120 ml) whole milk, room temperature preferred
Step-by-Step Instructions
- Preheat your oven to 350°F (175°C).
- Prepare the topping:
- Pour the melted butter into a 9.5-10″ pie plate or deep cake pan, ensuring it covers the bottom completely. Use a spoon or spatula to grease the sides.
- Sprinkle the brown sugar evenly over the butter.
- Arrange the pineapple slices on the bottom. Cut any leftover slices in half and arrange them up the sides of the pan.
- Place a maraschino cherry in the center of each pineapple ring and in any empty spaces. Set aside.
- Make the cake batter:
- In a medium-sized bowl, beat the butter and sugar until creamy and well-combined.
- Add the eggs one at a time, beating well after each addition.
- Stir in the vanilla extract.
- In a separate bowl, whisk together the flour, baking powder, and salt.
- Alternate adding the flour mixture and milk to the wet ingredients, starting and ending with the flour, and mixing until just combined after each addition (use a spatula to avoid overmixing).
- Assemble and bake:
- Pour the batter evenly over the prepared pineapple and cherry layer.
- Bake at 350°F (175°C) for 30 minutes. Then, loosely cover with foil and bake for an additional 15 minutes (total bake time: 45 minutes). The cake is done when a toothpick inserted into the center comes out mostly clean with a few crumbs.
- Cool and serve:
- Allow the cake to cool for 10-15 minutes, then carefully invert it onto a serving platter (be cautious as it will still be hot).
- Let it cool slightly before cutting, but enjoy while it’s still warm for the best taste.
Perfect Pairings: Serving Suggestions
This Pineapple Upside Down Cake is a star on its own, but it pairs beautifully with a scoop of vanilla ice cream or a dollop of whipped cream for an extra indulgent treat. For a tropical twist, serve it with a drizzle of coconut cream or a sprinkle of toasted coconut flakes. It’s also delightful with a cup of coffee or tea for a cozy dessert experience.
Keep It Fresh: Storage and Reheating Tips
Store leftover cake in an airtight container at room temperature for up to 2 days or in the fridge for up to 5 days. To reheat, warm individual slices in the microwave for 10-15 seconds or in a preheated oven at 300°F (150°C) for 5-10 minutes. This will bring back that warm, just-baked goodness!
Mix It Up: Recipe Variations
Feel free to get creative with this classic! Swap pineapple slices for canned peaches or mango for a different fruity twist. You can also add a splash of rum or coconut extract to the batter for a boozy or tropical flavor. For a nutty crunch, sprinkle chopped pecans or walnuts over the brown sugar layer before adding the fruit.
Quick Tips: Time-Saving Hacks
To save time, use pre-sliced pineapple rings and pat them dry with a paper towel to avoid excess moisture. If you’re in a rush, skip the cherry placement and simply scatter them over the pineapple layer. You can also prepare the cake batter in advance and store it in the fridge for up to 24 hours before baking.
Essential Tools: Equipment Guidance
A 9.5-10” pie plate or deep cake pan is ideal for this recipe to ensure even baking. A silicone spatula is great for spreading the batter without overmixing, and a toothpick or cake tester is essential for checking doneness. If you’re worried about sticking, consider using a non-stick pan or lining the bottom with parchment paper for easy release.
Pineapple Upside Down Cake
Ingredients
Topping
- ¼ cup salted butter melted
- ½ cup brown sugar light or dark (I usually use light) tightly packed
- 10 pineapple slices patted dry (a 20oz can is typically enough)
- maraschino cherries
Vanilla Cake
- ½ cup unsalted butter softened to room temperature
- ¾ cup granulated sugar
- 2 large eggs room temperature preferred
- 1 teaspoon vanilla extract
- 1 ½ cups all-purpose flour
- 1 ½ teaspoons baking powder
- ¼ teaspoon salt
- ½ cup whole milk room temperature preferred
Instructions
- Preheat oven to 350F (175C)
- Pour melted butter into 9.5-10″ pie plate or deep cake pan, make sure it entirely covers the bottom of the pan and use a spoon or spatula to grease the sides of the pan.
- Sprinkle brown sugar evenly over butter mixture. Arrange pineapple slices over the bottom of the pan, slice leftover slices in half and arrange up the sides of the pan, as seen in photo.
- Place cherries in center of pineapple rings and as desired in empty spaces. Set aside.
- To prepare vanilla cake, beat butter and sugar in medium-sized bowl until creamy and well-combined.
- Add eggs, beating one at a time until combined.
- Stir in vanilla extract.
- In a separate bowl, whisk together flour, baking powder, and salt.
- Alternate adding flour and milk to the wet ingredients, starting and ending with flour and mixing until just combined after each addition (I prefer to do this part by hand with a spatula to be sure not to overmix).
- Pour batter evenly over prepared cake pan over the pineapple/cherry layer. Bake on 350F (175C) for 30 minutes. At the 30 minute mark, loosely cover with foil and continue to bake (still on 350F/175C) for another 15 minutes, until a toothpick inserted in the center comes out mostly clean with few crumbs (total cook time for cake will be 45 minutes).
- Allow to cool for 10-15 minutes and then carefully invert cake onto serving platter (careful, it will still be very hot!).
- Allow to cool before cutting and enjoying, but don’t wait too long as this cake tastes wonderful (best!) warm from the oven!