Pineapple Upside-Down Cheesecake Recipe

ByLucy
Jump to Recipe· 4.5 from 10 reviews

If you’re like me and absolutely adore classic pineapple upside-down cake but crave something a little richer and creamier, you’re going to fall head over heels for this Pineapple Upside-Down Cheesecake Recipe. It’s like a tropical vacation wrapped up in a slice of silky cheesecake layered with moist pineapple cake and that caramelized pineapple topping we all love. Stick around—I’ll walk you through every step to ensure your dessert is flawless and unforgettable.

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Why This Recipe Works

  • Layered Delight: Combining pineapple upside-down cake with a creamy cheesecake layer gives you the best of both worlds—a tender cake with luscious texture.
  • Moist and Flavorful: Using pineapple juice and sour cream in both the cheesecake and cake batter keeps every bite moist and bursting with tropical flavor.
  • Water Bath Baking: Baking the cheesecake in a water bath ensures it stays smooth and crack-free, achieving that perfect creamy consistency we all want.
  • Beautiful Presentation: The caramelized pineapple rings and cherries make for a stunning finish you’ll be proud to serve.
Pineapple Upside-Down Cheesecake, tropical pineapple cheesecake, Easy pineapple dessert, creamy pineapple cake, caramelized pineapple topping - A two-layer round cake sits on a white marbled surface, with the bottom layer being a light brown sponge cake and the middle layer a thick, smooth cream that is pale yellow. The top layer is another light brown sponge with seven yellow pineapple rings evenly placed on it, each pineapple ring holding a small bright red cherry in the center. The cake looks moist and slightly shiny on top from the pineapple, and the overall shape is round and neatly stacked. In the background, there is a softly blurred aqua blue cloth, a white milk jug, and some out-of-focus flowers in soft pink and orange colors. Photo taken with an iphone --ar 2:3 --v 7 this …

Ingredients & Why They Work

This Pineapple Upside-Down Cheesecake Recipe brings together simple, wholesome ingredients that harmonize beautifully. Each component plays a crucial role, from that tangy cream cheese filling to the tender pineapple cake that cradles it.

Pineapple Upside-Down Cheesecake, tropical pineapple cheesecake, Easy pineapple dessert, creamy pineapple cake, caramelized pineapple topping - Flat lay of fresh cream cheese block, two whole brown eggs with clean shells, a small white bowl of granulated sugar, a small white bowl of light brown sugar, a small white bowl of sour cream, fourteen natural pineapple rings, fourteen bright red maraschino cherries, a small white bowl of melted unsalted butter, a small white bowl of pineapple juice, a small white bowl of milk, a small white bowl of vanilla extract, a white ceramic bowl with sifted all-purpose flour mixed with baking powder, baking soda, and salt, placed in perfect symmetry and realistic proportions on a clean white marble surface, soft natural light, photo taken with an iPhone, professional food photography style, fresh ingredients, white ceramic bowls, no bottles, no duplicates, no utensils, no packaging --ar 2:3 --v 7 --p m7354615311229779997
  • Cream Cheese: Using room-temperature cream cheese ensures a silky smooth cheesecake batter without lumps.
  • Granulated Sugar & Brown Sugar: Brown sugar creates that deep caramel flavor for the topping while granulated sugar sweetens the cheesecake filling evenly.
  • Eggs: Eggs give structure to the cheesecake and cake, helping both layers set perfectly.
  • Sour Cream: Adds moisture and a slight tang that balances the sweetness for a fresh taste.
  • Pineapple Juice: Boosts that vibrant pineapple flavor throughout the cheesecake and cake layers.
  • Vanilla Extract: It rounds out the flavors and brings warmth to each bite.
  • Butter: Melted butter in both the topping and cake batter ensures richness and tenderness.
  • Flour, Baking Powder, Baking Soda, Salt: These dry ingredients provide structure and leavening so your cake rises beautifully without being dense.
  • Pineapple Rings & Maraschino Cherries: Classic toppings that deliver nostalgia and that iconic look for a real crowd-pleaser.
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Note: You’ll find the complete list of ingredients, along with their exact measurements, in the printable recipe card at the bottom of this post.

Make It Your Way

One of the reasons I love this Pineapple Upside-Down Cheesecake Recipe is how easy it is to tweak. Whether you want it a little lighter or want to turn it into a show-stopping tropical extravaganza, there’s room to customize.

  • Variation: I’ve swapped in fresh pineapple instead of canned for an extra juicy touch. It gives a fresher flavor, especially when pineapples are in season.
  • Dairy-Free Option: If you need a lactose-free version, try cream cheese alternatives and coconut milk with some tweaks—I’ve done this successfully for a friend with dietary restrictions.
  • Spices: Adding a pinch of cinnamon or nutmeg into the cake batter adds a subtle warmth that beautifully complements the pineapple.
  • Mini Versions: You can make this in smaller pans or even cupcakes—great for parties or when you don’t want a huge dessert.

Step-by-Step: How I Make Pineapple Upside-Down Cheesecake Recipe

Step 1: Prep Your Cheesecake Base with Care

Start by greasing a 9-inch springform pan really well and wrapping it in heavy-duty foil—this is crucial because we will bake the cheesecake in a water bath to keep it smooth and crack-free. Then, whip the softened cream cheese with granulated sugar until it feels silky. I like to mix in the eggs one at a time, scraping down the bowl so everything blends evenly. Next, stir in the sour cream, pineapple juice, and vanilla extract until the mixture is perfectly smooth. Pour it into your prepared pan and set it in a large roasting pan.

Step 2: Bake the Cheesecake Gently in a Water Bath

Here’s where the magic happens: fill the roasting pan halfway with hot water—careful not to splash into the cheesecake pan! This slow, moist heat prevents cracking and ensures creaminess. Bake at 300°F for 45 minutes, then turn the oven off and let it rest inside for another 20 minutes. This gradual cooling helps the cheesecake set beautifully. When it’s done, take it out of the water bath, let it cool to room temperature, then cover and chill in the fridge for at least 8 hours, or even overnight. Trust me, this patience pays off.

Step 3: Make the Caramelized Pineapple Topping

While the cheesecake chills, grease two 9-inch cake pans and divide melted butter evenly between them. Sprinkle half the packed brown sugar into each pan—it’ll melt down and make that classic caramel base. Arrange pineapple slices and cherries on top in a pretty pattern. I love how familiar this looks, it instantly makes me nostalgic for family gatherings.

Step 4: Whip Up the Pineapple Cake Batter

Mix together flour, baking powder, baking soda, and salt. In a separate bowl, whisk melted butter with light brown and granulated sugars until smooth. Then, add the egg, sour cream, milk, pineapple juice, and vanilla—this combo keeps the cake tender and moist. Stir the wet ingredients into the dry ingredients gently until everything is just combined—no overmixing! Pour half the batter into each prepared pan over the pineapple and cherries. Bake at 350°F for 25-30 minutes until golden and a toothpick comes out clean.

Step 5: Assemble and Serve with a Smile

Once your cake layers have cooled for about 10 minutes, carefully invert one onto your serving plate and the other onto a flat surface like a cutting board. Gently remove the cheesecake from its pan—an offset spatula helps here—and place it on top of the first cake layer. Then, stack the second cake layer atop the cheesecake to create that irresistible triple-layer masterpiece. You can serve right away or chill for a few hours to let the flavors marry. I usually garnish with whipped cream for a touch of creaminess and flair.

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Tips from My Kitchen

  • Room Temperature Matters: I can’t stress enough how important it is that your cream cheese, eggs, and sour cream are at room temperature before mixing—they blend smoother and prevent lumps.
  • Secure the Water Bath: Wrapping the springform pan in heavy-duty foil prevents water from seeping into your cheesecake—learned that the hard way!
  • Don’t Overmix: Especially with the cheesecake batter, mix on low speed to avoid too much air that leads to cracking.
  • Inverting with Care: When flipping the pineapple upside-down cakes, do it gently to keep your pineapple and cherry patterns perfectly intact.

How to Serve Pineapple Upside-Down Cheesecake Recipe

Pineapple Upside-Down Cheesecake, tropical pineapple cheesecake, Easy pineapple dessert, creamy pineapple cake, caramelized pineapple topping - The image shows a slice of pineapple upside-down cake being lifted by a fork. The cake slice has three layers: the top yellow layer is a round pineapple ring with a bright red cherry in the center, the middle layer is light and creamy with a smooth texture, and the bottom layer is a golden brown cake with small chunks of pineapple embedded. The full cake below has similar layers and looks moist and soft. The scene is set on a white marbled surface, with a blurry background featuring pink flowers and a glass bottle of milk. Photo taken with an iphone --ar 2:3 --v 7

Garnishes

Personally, I love topping this dessert with a dollop of freshly whipped cream—maybe just a hint of vanilla or a sprinkle of toasted coconut flakes. Sometimes, a little extra maraschino cherry on top adds that classic pop of color and sweetness that ties everything together beautifully.

Side Dishes

This dessert stands out on its own, but if you want to serve it alongside something, fresh tropical fruit salad or a scoop of creamy vanilla ice cream are fantastic companions. For coffee lovers, a strong espresso cuts through the richness and complements the tropical flavors.

Creative Ways to Present

For special occasions, I’ve tried serving individual slices layered in glass jars—it makes for a gorgeous presentation, and guests love the portion control. Another fun idea is turning it into a trifle by layering crumbled cake, cheesecake filling, and pineapple chunks in clear dishes, perfect for summer parties.

Make Ahead and Storage

Storing Leftovers

I wrap leftover slices tightly in plastic wrap or place them in airtight containers and keep them refrigerated. They stay fresh and delicious for up to 4 days. It’s an easy treat to grab for afternoon snacks or a quick dessert.

Freezing

Freezing this cheesecake works well if you wrap it securely with plastic wrap and aluminum foil to protect it from freezer burn. When I’ve frozen slices, I find thawing them overnight in the fridge preserves the texture best. Just keep in mind the pineapple cake layers can get a little softer after freezing but still taste amazing.

Reheating

I don’t recommend reheating the cheesecake too much, but if you want a warm slice, a quick 15-second zap in the microwave helps bring out those luscious flavors without melting the layers. Otherwise, serve chilled for the best texture.

FAQs

  1. Can I use canned pineapple for this Pineapple Upside-Down Cheesecake Recipe?

    Absolutely! Both canned and fresh pineapple work well in this recipe. Just be sure to drain canned pineapple slices well to avoid excess moisture, which can affect the cake’s texture. Fresh pineapple gives a slightly brighter flavor but either option tastes delicious.

  2. Why do I need to bake the cheesecake in a water bath?

    Baking the cheesecake in a water bath helps regulate the oven’s heat around the pan, preventing the cheesecake from drying out or cracking. It keeps the texture creamy and smooth, which is key for this dessert’s luxurious feel.

  3. Can I make this recipe ahead of time?

    Yes! In fact, it’s best when made ahead since the cheesecake needs several hours to chill and set properly. You can assemble it the night before and store it in the refrigerator until you’re ready to serve.

  4. How do I keep the pineapple and cherries from sticking when I invert the cake?

    Using melted butter and brown sugar as a base before adding the fruit creates a caramelized layer that helps the pineapple and cherries release easily when flipped. Also, make sure the cake has cooled slightly before inverting to avoid tearing.

Final Thoughts

This Pineapple Upside-Down Cheesecake Recipe has become a family favorite, and I love how it brings something new yet comfortingly familiar to the table. Whether you’re baking it for a special occasion or simply as an everyday treat, it’s sure to impress. Give it a try—you might just find a new signature dessert that everyone asks for again and again!

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Pineapple Upside-Down Cheesecake Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.5 from 10 reviews
  • Author: Lucy
  • Prep Time: 20 minutes
  • Cook Time: 1 hour 35 minutes
  • Total Time: 7 hours 40 minutes
  • Yield: 12 servings
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
Print Recipe

Description

This Copycat Pineapple Upside Down Cheesecake combines the rich creaminess of a classic cheesecake with the sweet, caramelized flavors of pineapple upside-down cake. Featuring a buttery pineapple and cherry topping layered between two moist cake layers and a luscious pineapple-infused cheesecake center, this dessert is perfect for special occasions or indulgent treats.

Ingredients

Pineapple Cheesecake

  • 16 ounces cream cheese room temp
  • 1/2 cup granulated sugar
  • 2 large eggs
  • 1/2 cup sour cream
  • 2 tablespoons pineapple juice
  • 1 teaspoon vanilla extract

Pineapple Upside-Down Cake Topping

  • 1/2 cup unsalted butter melted
  • 1 cup packed light brown sugar
  • 14 slices canned or fresh pineapple rings
  • 14 maraschino cherries

Pineapple Upside-Down Cake Batter

  • 1 1/2 cup + 3 tablespoons all-purpose flour sifted
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter melted
  • 3/4 cup light brown sugar packed
  • 1/4 cup granulated sugar
  • 1 large egg
  • 1/4 cup sour cream
  • 1/2 cup milk
  • 1/4 cup pineapple juice
  • 1 tablespoon vanilla extract

Instructions

  1. Prepare the Cheesecake Batter: Preheat the oven to 325°F. Grease a 9-inch springform pan, wrap the outside with heavy-duty foil to prevent leaks, and set aside. Using an electric hand mixer, whip the cream cheese and 1/2 cup granulated sugar together until smooth. Add the eggs one at a time, mixing well after each addition and scraping down the sides as needed. Mix in the sour cream, pineapple juice, and vanilla extract until the batter is completely smooth.
  2. Bake the Cheesecake: Pour the cheesecake batter into the prepared springform pan and place it inside a larger roasting pan. Reduce the oven temperature to 300°F. Carefully pour hot water into the roasting pan until it comes halfway up the sides of the springform pan to create a water bath. Bake for 45 minutes, then turn off the oven and leave the cheesecake inside for an additional 20 minutes to set. Remove the cheesecake from the oven and water bath, then cool on the counter to room temperature. Cover with plastic wrap and refrigerate for at least 8 hours or overnight.
  3. Make the Pineapple Upside-Down Topping: Divide the melted 1/2 cup unsalted butter evenly between two 9-inch cake pans. Sprinkle 1/2 cup light brown sugar into each pan over the butter. Arrange 7 pineapple slices and 7 maraschino cherries decoratively in each pan on top of the sugar mixture. Set aside.
  4. Prepare the Cake Batter: Preheat the oven to 350°F. In a large bowl, whisk together the sifted all-purpose flour, baking powder, baking soda, and salt. In a separate medium bowl, whisk the melted butter with 3/4 cup packed light brown sugar and 1/4 cup granulated sugar until smooth. Add the egg, sour cream, milk, pineapple juice, and vanilla extract to the wet mixture and whisk until fully combined. Pour the wet ingredients into the dry mix and stir gently until just combined with no lumps.
  5. Bake the Cake Layers: Pour the cake batter evenly into the two prepared pans over the pineapple and cherries, smoothing the top carefully so as not to disturb the arrangement. Bake each pan for 30 minutes until a toothpick inserted into the cake comes out clean and the tops are golden brown. Let the cakes cool in the pans on wire racks for 10 minutes.
  6. Assemble the Cake: Carefully invert one cake onto a flat surface like a cutting board and the other cake onto the serving plate, revealing the pineapple and cherry topping. Remove the cheesecake from the springform pan by running an offset spatula around the edges to loosen it and gently lift it off the pan bottom. Place the cheesecake layer on top of the first inverted cake layer. Then place the second inverted cake layer on top of the cheesecake. Garnish with whipped cream if desired. Serve immediately or refrigerate until ready to serve.

Notes

  • Room Temperature Ingredients: Ensure cream cheese, eggs, and sour cream are at room temperature to achieve a smooth cheesecake texture.
  • Water Bath: Baking the cheesecake in a water bath prevents cracks and keeps it creamy and moist.
  • Proper Mixing: Mix the cheesecake batter on low speed to avoid incorporating excess air, which can cause cracks during baking.
  • Cool Completely: Allow the cheesecake to cool fully on the counter or on a wire rack before refrigerating to help set properly.
  • Invert Carefully: When flipping the pineapple upside-down cake layers, be gentle to keep the pineapple slices and cherries intact.
  • Chill Time: Let the assembled cake chill in the refrigerator for a few hours before serving to meld flavors and improve texture.

Nutrition

  • Serving Size: 1 slice
  • Calories: 450 kcal
  • Sugar: 38 g
  • Sodium: 280 mg
  • Fat: 25 g
  • Saturated Fat: 15 g
  • Unsaturated Fat: 9 g
  • Trans Fat: 0 g
  • Carbohydrates: 45 g
  • Fiber: 1 g
  • Protein: 6 g
  • Cholesterol: 110 mg

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