Get ready to fall in love with a show-stopping dessert: Pineapple Upside-Down Cheesecake. With its vivid crown of caramelized pineapple rings, maraschino cherries, and a luscious swirl of creamy cheesecake atop a buttery cake base, this treat takes the nostalgia of classic pineapple upside-down cake and gives it a dreamy, cheesecake twist. Each bite is a symphony of buttery, tangy, and sweet flavors that’s simply unforgettable. If you’re looking for a spectacular centerpiece for your next gathering, or you just want a slice of sunshine at home, this Pineapple Upside-Down Cheesecake absolutely delivers.
Ingredients You’ll Need
Let’s talk about what goes into this decadent dessert. Each of these simple ingredients plays a special role, whether it’s adding richness, a tropical punch, color, or that classic old-fashioned vibe. Here’s what you’ll need and why every one counts:
- Unsalted butter (for topping and cake): Gives the cake its trademark moistness and helps caramelize the pineapple for maximum flavor.
- Light brown sugar: Melts beautifully to create a caramel base, complementing the fruity pineapple topping.
- Canned pineapple rings: Offer a pop of tropical sweetness and visual flair—plus, they hold their shape well when baked.
- Maraschino cherries: Add a nostalgic burst of color and just the right touch of extra sweetness.
- Cream cheese: Forms the creamy, tangy heart of the cheesecake layer—be sure it’s softened for a silky texture.
- Granulated sugar: Essential for balancing tang and sweetness in both the cake and the cheesecake layers.
- Large eggs: Bind each layer while adding richness to the custardy, souffle-like structure.
- Vanilla extract: Deepens the flavors throughout the cake, cheesecake, and even the aroma.
- Sour cream: Lends tang and a velvety finish to the cheesecake.
- All-purpose flour: The foundation for the cake layer, giving structure and lightness.
- Baking powder: Adds that essential lift, so the cake rises up the sides of the pan for a lovely layered effect.
- Salt: Brightens and balances all the flavors, so no layer tastes flat.
- Whole milk: Ensures the cake layer is tender, not dry.
How to Make Pineapple Upside-Down Cheesecake
Step 1: Prepare the Pan
Start by preheating your oven to 325°F. Use a 9-inch springform pan for effortless releasing—this is a layered dessert, after all! Tightly wrap the bottom of the pan with foil so nothing leaks out during baking. Lightly grease the pan and, if you have some on hand, place a round of parchment at the bottom. This little trick makes flipping and slicing your Pineapple Upside-Down Cheesecake so much easier later on.
Step 2: Make the Pineapple Topping
Pour the melted butter into the bottom of your prepared pan. Sprinkle the brown sugar evenly over the butter, letting it form a luscious layer of caramel. Now, lay out the pineapple rings in a single, overlapping circle. Drop a maraschino cherry into the center of each ring. This step isn’t just for looks—the fruit will soften into the caramel and infuse the cheesecake as it bakes, giving your Pineapple Upside-Down Cheesecake its signature flavor and appeal.
Step 3: Whip up the Cheesecake Layer
In a large bowl, beat the softened cream cheese with granulated sugar until your mixture is fluffy and totally smooth. Add eggs, one at a time, mixing well after each addition. Blend in your vanilla and sour cream until just incorporated. Don’t overmix! Spread this creamy cheesecake filling gently over your fruit topping, smoothing the top so the cheesecake bakes evenly and holds its shape atop the pineapple.
Step 4: Prepare the Cake Layer
Grab a second bowl, and cream together the soft butter and sugar until pale and light. Beat in your eggs and vanilla, mixing well so everything is silky. In a third bowl, whisk together the flour, baking powder, and salt. Now, add the dry ingredients to your wet mixture in stages, alternating with milk (start and finish with the flour mix). The result is a light, fluffy batter. Carefully spoon or dollop this cake batter over the cheesecake, then gently spread it out so it covers the cheesecake without disturbing it.
Step 5: Bake and Chill
Place the springform pan on a sturdy baking sheet to catch any drips. Bake your Pineapple Upside-Down Cheesecake for 60 to 70 minutes. You want the top to be golden brown, and a toothpick inserted into the cake layer should come out clean. Let it cool completely in the pan—don’t rush this part! Refrigerate for at least 4 hours, or preferably overnight, so every layer sets up beautifully and the flavors marry together.
Step 6: Unmold and Flip
Once chilled, run a thin knife around the edge of the pan to loosen it. Carefully open the springform latch, then invert the whole cheesecake onto your serving plate. (If you used parchment, this is even easier!) Stand back and admire exactly why Pineapple Upside-Down Cheesecake is a true showstopper—the glossy pineapple and cherries will be perfectly caramelized and ready to dazzle.
How to Serve Pineapple Upside-Down Cheesecake
Garnishes
A slice of Pineapple Upside-Down Cheesecake is swoon-worthy on its own, but a billow of freshly whipped cream makes it positively irresistible. A few extra maraschino cherries or a sprinkle of toasted coconut add a festive touch. For a hint of tropical brightness, a twist of lime zest works beautifully.
Side Dishes
Serve this cheesecake with a crisp fruit salad—think mango, kiwi, or even berries—for a refreshing contrast. Coffee or a glass of sparkling wine are fantastic companions, balancing the dessert’s richness with a little acidity and fizz. If you’re celebrating, a scoop of vanilla or coconut ice cream on the side makes things extra special.
Creative Ways to Present
For a true wow factor, serve mini Pineapple Upside-Down Cheesecakes in individual ramekins. You can also create a build-your-own dessert platter with small squares of the cheesecake, bowls of whipped cream, crushed pineapple, and cherries, so everyone can top theirs just the way they like. Or, stack thin slices for dramatic layers on dessert plates and drizzle with a bit of pineapple syrup.
Make Ahead and Storage
Storing Leftovers
Place any Pineapple Upside-Down Cheesecake leftovers in an airtight container and keep them in the refrigerator for up to 4 days. The cake and cheesecake layers remain moist and flavorful, and the topping stays glossy. For the neatest slices, use a clean, sharp knife—and don’t forget to wipe between cuts!
Freezing
You can definitely freeze Pineapple Upside-Down Cheesecake! Wrap individual slices or the whole cake (well chilled) in plastic wrap, then aluminum foil. Store in the freezer for up to a month. When you’re ready to enjoy, thaw it overnight in the fridge. This makes it easy to prep ahead for parties or unexpected cravings.
Reheating
Generally, this dessert is best served well chilled or at cool room temperature, so reheating isn’t necessary. If you do want it slightly warmer, let a slice sit out at room temperature for about 20 minutes. Try to avoid the microwave, as it can quickly melt the delicate cheesecake layer.
FAQs
Can I use fresh pineapple instead of canned?
Yes, you can! Fresh pineapple brings a wonderful tang and brightness to the topping. Just make sure to slice it thinly and pat it dry with paper towels before arranging it in the pan, as fresh pineapple can release more juice when baked.
What makes Pineapple Upside-Down Cheesecake different from the classic cake?
The addition of a creamy cheesecake layer sandwiched between the pineapple topping and the buttery cake base transforms the classic into something extra special. You get the best of both worlds: tropical sweetness, creamy tang, and a soft cake, all in one fabulous slice.
How do I prevent the cheesecake from cracking?
Cracks are less of an issue in Pineapple Upside-Down Cheesecake because the topping covers the surface, but for a perfectly smooth result, don’t overmix the batter, and bake at a stable, moderate temperature. Cooling the cake gradually and chilling it thoroughly also helps maintain a flawless layer.
Can I make this gluten-free?
Absolutely! Swap the all-purpose flour for your favorite gluten-free blend. Check that your baking powder and other ingredients are also certified gluten-free, and you’ll have a dessert that everyone can enjoy.
Is it possible to reduce the sugar in the recipe?
You can reduce the granulated sugar in both the cake and cheesecake layers by about 1/4 without affecting the structure, but the topping relies on sugar for caramelization, so keep that as is for the best result. The flavor will still be delightfully sweet and tropical.
Final Thoughts
I hope you’re feeling inspired to whip up this Pineapple Upside-Down Cheesecake for your next celebration or cozy night in. It’s the kind of dessert that never fails to impress—bright, creamy, nostalgic, and an absolute joy to share. If you try it, be prepared for lots of compliments and (quite possibly) requests for the recipe. Happy baking!
Print
Pineapple Upside-Down Cheesecake Recipe
- Prep Time: 30 minutes
- Cook Time: 1 hour 10 minutes
- Total Time: 1 hour 40 minutes (plus chilling)
- Yield: 10 slices
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
Indulge in the delightful combination of a classic pineapple upside-down cake and a creamy cheesecake with this Pineapple Upside-Down Cheesecake recipe. A luscious treat perfect for any occasion!
Ingredients
For the pineapple topping:
- 1/4 cup unsalted butter (melted)
- 1/2 cup light brown sugar (packed)
- 6–7 canned pineapple rings (drained)
- 6–7 maraschino cherries
For the cheesecake layer:
- 2 (8 oz) packages cream cheese (softened)
- 1/2 cup granulated sugar
- 2 large eggs
- 1 tsp vanilla extract
- 1/4 cup sour cream
For the cake layer:
- 1/2 cup unsalted butter (softened)
- 1/2 cup granulated sugar
- 2 large eggs
- 1 tsp vanilla extract
- 1 1/4 cups all-purpose flour
- 1 1/2 tsp baking powder
- 1/4 tsp salt
- 1/2 cup whole milk
Instructions
- Make the topping: Pour melted butter into the bottom of the pan and sprinkle with brown sugar. Arrange pineapple rings over the sugar, placing a cherry in the center of each ring. Set aside.
- Make the cheesecake layer: In a large bowl, beat cream cheese and sugar until smooth and fluffy. Add eggs one at a time, mixing well after each. Mix in vanilla and sour cream until just combined. Pour over the pineapple layer and smooth the top.
- Make the cake layer: In another bowl, cream butter and sugar until light. Add eggs and vanilla, beating well. In a separate bowl, whisk together flour, baking powder, and salt. Add dry ingredients to wet mixture, alternating with milk, beginning and ending with flour. Carefully spoon the batter over the cheesecake layer and gently spread evenly.
- Bake for 60–70 minutes, or until a toothpick inserted into the cake layer comes out clean and the top is golden. Let cool completely in the pan, then refrigerate for at least 4 hours or overnight. To serve, run a knife around the edge and carefully invert onto a plate.
Notes
- Use parchment on the bottom of the pan for easier release.
- This cheesecake-cake hybrid is best chilled overnight before flipping.
- Serve with whipped cream if desired.
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