If you have a craving for something that feels both nostalgic and irresistibly indulgent, this Pineapple Upside-Down Cheesecake Recipe is going to be your new best friend. Combining the classic tropical charm of caramelized pineapple and cherries with the rich, creamy texture of cheesecake creates a dessert that’s as visually stunning as it is delicious. It’s a perfect celebration cake or a sweet ending to any family meal that will surely have everyone asking for seconds.

Pineapple Upside-Down Cheesecake Recipe - Recipe Image

Ingredients You’ll Need

Every ingredient in this recipe plays an important role in delivering layers of flavor and texture that make this dessert truly special. From the crunchy, buttery graham cracker crust to the luscious cream cheese filling and the glossy caramelized pineapple topping, these simple items come together to create magic.

1 1/2 cups graham cracker crumbs: This forms the crunchy, slightly sweet base that balances the smooth cheesecake.
1/4 cup granulated sugar: Adds sweetness to the crust for a flawless balance.
6 tablespoons melted butter: Binds the crust crumbs and adds richness.
1/2 cup packed brown sugar: Essential for that luscious caramel sauce at the bottom, giving the topping its deep flavor.
1/4 cup unsalted butter: Melted with brown sugar to create the caramel that coats the pineapple.
10–12 pineapple rings (canned or fresh): The star of the topping bringing sweetness and tropical freshness.
Maraschino cherries (one for each ring): A pop of color and a sweet surprise in every bite.
3 (8 oz) blocks cream cheese, softened: The silky base of the cheesecake filling.
1 cup granulated sugar: Sweetens the creamy filling to perfection.
1/2 cup sour cream: Adds moisture and a subtle tanginess that keeps the cheesecake from feeling too heavy.
1 teaspoon vanilla extract: Enhances the overall flavor with warm, inviting notes.
3 large eggs: Provide structure and creaminess when baked just right.
1/2 cup crushed pineapple (drained well): Infuses the cheesecake with bursts of pineapple flavor throughout.

How to Make Pineapple Upside-Down Cheesecake Recipe

Step 1: Prepare the Pineapple Topping

Start by melting butter and brown sugar together in a small saucepan over medium heat until it begins to bubble. This simple caramel is the foundation of the luscious topping. Pour this golden mixture into the bottom of your greased 9-inch springform pan. Then, carefully arrange the pineapple rings on top of the caramel, placing a maraschino cherry in the center of each ring. This visual setup will create a jaw-dropping presentation once flipped later.

Step 2: Make the Crust

Next, combine the graham cracker crumbs, granulated sugar, and melted butter in a bowl until fully mixed. This mixture will create a delicious crunchy crust with just the right amount of sweetness. Press it evenly over the pineapple rings and slightly up the sides of the pan to hold everything in place. Pop the crusted pan into the fridge to chill and firm while you focus on the cheesecake filling.

Step 3: Preheat the Oven

Preheat your oven to 325°F (160°C). To protect your cheesecake from water leakage during baking, wrap the outside of the springform pan with aluminum foil securely. Then place your springform pan inside a larger baking dish that will hold the hot water for the water bath.

Step 4: Prepare the Cheesecake Filling

In a large mixing bowl, beat the softened cream cheese with sugar until perfectly smooth and creamy. Incorporate the sour cream and vanilla extract for moisture and subtle flavor depth. Add the eggs one at a time, beating just enough to combine them without overmixing, which keeps the texture silky and dense. Gently fold in the drained crushed pineapple to infuse every bite with pineapple goodness.

Step 5: Assemble and Bake

Pour the creamy cheesecake filling over your chilled crust and pineapple layer. Place the springform pan in the larger baking dish and pour hot water halfway up its sides to create a gentle, even cooking environment. Bake for 60 to 70 minutes or until the center is just set — the cheesecake should still have a slight jiggle but not be liquid.

Step 6: Cooling and Chilling

Once out of the oven, remove the cheesecake from the water bath and let it cool completely at room temperature. This slow cooling step helps prevent cracks and ensures perfect texture. After cooling, refrigerate the cheesecake for at least 4 hours or overnight to let the flavors meld beautifully.

Step 7: Flip and Serve

Run a knife gently around the edges of the cake to loosen it from the sides of the pan. Then carefully invert the springform pan onto your favorite serving platter so the stunning pineapple and cherry topping is revealed, glistening and caramelized. Slice generously and get ready to impress your guests or treat yourself to a slice of heaven.

How to Serve Pineapple Upside-Down Cheesecake Recipe

Garnishes

This cheesecake shines best on its own but you can elevate it with a few thoughtful garnishes. Consider a light dusting of toasted coconut flakes to add a tropical crunch or some fresh mint leaves for a refreshing pop of color and aroma. A drizzle of caramel sauce or extra maraschino cherries around the plate will add a playful touch.

Side Dishes

Pair your Pineapple Upside-Down Cheesecake Recipe with bright, complementary sides like a chilled tropical fruit salsa or a simple vanilla bean ice cream scoop. The creaminess of the ice cream beautifully contrasts the caramel topping while fresh fruits keep things light and balanced.

Creative Ways to Present

For a fun twist, try making individual mini cheesecakes in muffin tins with the same pineapple upside-down topping. This makes serving easier for parties and everyone gets their own personal treat. Another idea is serving slices alongside a sparkling tropical cocktail or a cup of freshly brewed coffee to turn dessert into a full experience.

Make Ahead and Storage

Storing Leftovers

Your Pineapple Upside-Down Cheesecake Recipe keeps wonderfully in the refrigerator for up to 4 days. Store it tightly covered with plastic wrap or in an airtight container to maintain moisture and keep the topping glossy and fresh.

Freezing

If you want to keep this beauty longer, you can freeze individual slices wrapped well in parchment and aluminum foil. For best taste and texture, thaw them overnight in the fridge before serving. Keep in mind the topping may soften slightly after freezing but will still taste amazing.

Reheating

Because this is a chilled cheesecake, reheating is not necessary. However, if desired, allow slices to sit at room temperature for 15-20 minutes to soften slightly before serving for the best mouthfeel and flavor release.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple rings and crushed pineapple add an extra layer of tropical freshness. Just make sure to drain excess juice well to avoid making the crust soggy.

Do I have to use a water bath when baking?

Using a water bath helps the cheesecake bake gently and evenly, preventing cracks and dryness. It’s a key step to get that smooth, creamy texture every time.

How long should I chill the cheesecake before serving?

For best texture and flavor, chill the cheesecake for at least 4 hours, but overnight chilling is ideal. This resting time allows the cheesecake to firm up perfectly.

Can I make this recipe gluten-free?

Yes! Substitute the graham cracker crumbs with a gluten-free alternative or crushed nuts to keep the delicious crust while accommodating dietary needs.

What’s the best way to slice this cheesecake neatly?

Use a sharp knife dipped briefly in hot water and wiped dry between slices. This prevents sticking and helps you get clean, beautiful slices every time.

Final Thoughts

There’s something undeniably joyful about this Pineapple Upside-Down Cheesecake Recipe that makes it worth every minute of preparation. It’s a dessert that combines elegance with a comforting tropical twist, perfect for celebrations or simply treating yourself after a long day. I can’t wait for you to try this recipe and create your own special moments with its luscious flavors and stunning presentation.

Pineapple Upside-Down Cheesecake Recipe

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3.8 from 40 reviews

Author: admin
Total Time: 5 hours 40 minutes
Yield: 12 servings 1x

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Description

This Pineapple Upside-Down Cheesecake combines the classic tropical flavors of caramelized pineapple and cherries with a rich, creamy cheesecake. Featuring a buttery graham cracker crust atop a luscious pineapple-infused cream cheese filling, this dessert is baked in a water bath for perfect texture and a beautiful presentation when flipped. Ideal for special occasions or a unique twist on traditional cheesecake favorites.

Ingredients

Scale

Pineapple Topping

1/2 cup packed brown sugar
1/4 cup unsalted butter
10–12 pineapple rings (canned or fresh)
Maraschino cherries (one for each ring)

Crust

1 1/2 cups graham cracker crumbs
1/4 cup granulated sugar
6 tablespoons melted butter

Cheesecake Filling

3 (8 oz) blocks cream cheese, softened
1 cup granulated sugar
1/2 cup sour cream
1 teaspoon vanilla extract
3 large eggs
1/2 cup crushed pineapple (drained well)

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Instructions

Prepare the pineapple topping. In a small saucepan over medium heat, melt the butter and brown sugar together, stirring occasionally until the mixture bubbles and caramelizes. Immediately pour this caramel into the bottom of a greased 9-inch springform pan. Arrange the pineapple rings neatly on top of the caramel, then place a maraschino cherry in the center of each pineapple ring. Set this assembly aside while preparing the crust.
Make the crust. In a mixing bowl, combine the graham cracker crumbs, granulated sugar, and melted butter. Stir until all crumbs are evenly coated with butter. Press this crumb mixture firmly over the pineapple rings and caramel in the pan, extending slightly up the sides to form a crust layer. Place the pan in the refrigerator to chill while you prepare the filling; this helps the crust set properly.
Preheat the oven. Set your oven to 325°F (160°C). To prevent water from leaking into the cheesecake during baking, wrap the outside of your springform pan with aluminum foil tightly. Then, place the pan inside a larger baking dish that will accommodate a water bath.
Make the cheesecake filling. Using a large bowl and a mixer, beat the softened cream cheese and granulated sugar together until completely smooth and creamy. Add the sour cream and vanilla extract, mixing well until incorporated. Add the eggs one at a time, beating each just until combined to avoid overmixing. Gently fold in the well-drained crushed pineapple, distributing it evenly.
Assemble and bake. Pour the cheesecake filling over the chilled crust and pineapple topping in the springform pan. Carefully place the pan into the larger baking dish, then pour hot water into the larger dish until it comes about halfway up the sides of the springform pan to create a water bath. Bake the cheesecake for 60 to 70 minutes, or until the center is just set but still slightly jiggly. This gentle baking method helps ensure a smooth, creamy texture without cracking.
Cool and chill. Remove the springform pan from the water bath and let the cheesecake cool completely at room temperature. Once cooled, refrigerate the cheesecake for at least 4 hours, or preferably overnight, to allow it to fully set and develop flavor.
Flip and serve. To serve, carefully run a knife around the edges of the pan to loosen the cheesecake. Place a serving platter on top of the pan and invert it so that the pineapple rings and cherries are on top, creating the classic upside-down presentation. Slice and enjoy this beautiful, indulgent dessert.

Notes

Use room temperature cream cheese for a smoother filling without lumps.
Ensure the crushed pineapple is well-drained to prevent excess moisture in the cheesecake.
Wrapping the springform pan with foil is crucial to prevent water leaks during the water bath bake.
The water bath baking method gives a silky, crack-free cheesecake texture.
Allowing the cheesecake to chill overnight improves slicing and flavor development.
Pineapple rings can be fresh or canned; if fresh, grill slightly for extra flavor before caramelizing if desired.

Prep Time: 40 minutes
Cook Time: 1 hour 10 minutes
Category: Dessert
Method: Baking
Cuisine: American