If you adore tropical flavors and creamy desserts, then this Pineapple Upside-Down Cheesecake Recipe is about to become your new favorite indulgence. It brilliantly combines the caramelized fruit charm of the classic pineapple upside-down cake with the luscious richness of cheesecake, creating a dessert that’s both visually stunning and decadently delicious. Each bite boasts a perfect harmony of buttery graham cracker crust, tangy cream cheese filling, and sweet pineapple topped with maraschino cherries. Whether you’re preparing a special occasion treat or simply craving something extraordinary, this recipe is guaranteed to impress and satisfy every sweet tooth.

Ingredients You’ll Need
Gathering your ingredients for this Pineapple Upside-Down Cheesecake Recipe is wonderfully straightforward, yet each one plays a crucial role in building layers of flavor and texture that make this dessert unforgettable.
- Graham cracker crumbs: Provide a crunchy, buttery base that supports the cheesecake beautifully.
- Granulated sugar: Used twice to sweeten both the crust and the creamy filling perfectly.
- Melted butter: Adds richness to the crust and caramel topping, enhancing depth.
- Brown sugar: Melts into a luscious caramel providing that classic pineapple upside-down sweetness.
- Unsalted butter: Helps create the caramel base under the pineapple so it’s gooey, not burnt.
- Pineapple rings: Fresh or canned, the star of the show adding juicy, tropical brightness.
- Maraschino cherries: Bright red centers that make each pineapple ring pop visually and add a hint of fruity sweetness.
- Cream cheese (softened): The main component of the cheesecake layer, delivering smooth, tangy richness.
- Sour cream: Brings moistness and a subtle tang that balances the sweetness.
- Vanilla extract: Enhances the overall flavor profile with warming notes.
- Eggs: Bind the cheesecake filling into a silky, firm consistency without cracking.
- Crushed pineapple (drained): Adds moist texture and reinforces the tropical theme within the cheesecake.
How to Make Pineapple Upside-Down Cheesecake Recipe
Step 1: Create the Pineapple Caramel Base
Start by melting unsalted butter with brown sugar in a small saucepan over medium heat, allowing the mixture to bubble slightly into a sticky caramel sauce. Pour this sweet base into the bottom of your greased 9-inch springform pan. Then arrange your pineapple rings neatly over the caramel and nestle a maraschino cherry right in the middle of each ring. This arrangement sets up the iconic look and flavor that defines the Pineapple Upside-Down Cheesecake Recipe.
Step 2: Prepare the Graham Cracker Crust
In a mixing bowl, combine graham cracker crumbs, granulated sugar, and melted butter until the mixture resembles wet sand. Press this crumbly mixture evenly over the pineapple layer, making sure to line the pan’s sides slightly as well. This crust chills in the fridge, allowing it to firm up and lock in all those buttery notes before the creamy filling is added.
Step 3: Preheat and Prepare the Oven Setup
Set your oven to 325°F (160°C). To protect your cheesecake from water seeping in during baking, wrap the outside of the springform pan tightly with aluminum foil. Then place the wrapped pan into a larger baking dish, which you’ll fill with hot water for a gentle water bath. This slow, even bake helps prevent cracks and keeps the cheesecake luxuriously smooth.
Step 4: Mix the Cheesecake Filling
Beat softened cream cheese and granulated sugar together until totally smooth and creamy. Add in the sour cream and vanilla, mixing again until blended. Then, add eggs one at a time, beating just enough to combine without overmixing. Finally, fold in the well-drained crushed pineapple for bursts of tropical flavor throughout. This filling is the decadent heart of the Pineapple Upside-Down Cheesecake Recipe.
Step 5: Assemble and Bake the Cheesecake
Carefully pour the cheesecake mixture over your chilled graham cracker crust, making sure it spreads evenly. Place your springform pan into the prepared water bath and bake for 60 to 70 minutes. You’ll know it’s ready when the edges are set but the center still jiggles slightly—a perfect indicator for creamy perfection.
Step 6: Cool and Chill Thoroughly
Once baked, remove the cheesecake from the water bath and let it cool completely on your countertop. Then refrigerate for at least four hours, preferably overnight. This chilling step is essential for the layers to firm up and the flavors to meld beautifully in this Pineapple Upside-Down Cheesecake Recipe.
Step 7: Flip and Serve
To reveal the iconic pineapple and cherry topping, carefully run a knife around the edges to loosen the cheesecake from the pan. Then invert it onto a large serving platter so that the caramelized fruit is gloriously displayed on top. Slice generously and get ready to enjoy each heavenly bite.
How to Serve Pineapple Upside-Down Cheesecake Recipe

Garnishes
For a little extra flair, top your cheesecake with freshly whipped cream infused with a hint of vanilla or a sprinkle of toasted coconut flakes. They add delightful texture and highlight the tropical notes in the Pineapple Upside-Down Cheesecake Recipe wonderfully.
Side Dishes
Pair the cheesecake with a light, fruity salad or a scoop of vanilla bean ice cream. These accompaniments complement the richness of the dessert while keeping the palate refreshed and ready for another slice.
Creative Ways to Present
Try serving individual portions in clear glasses layered with pineapple chunks and caramel drizzle for an elegant touch. Or turn it into mini cheesecakes using ramekins for intimate gatherings, bringing the same magic of the Pineapple Upside-Down Cheesecake Recipe in a delightful single-serving experience.
Make Ahead and Storage
Storing Leftovers
Store any leftover cheesecake tightly covered with plastic wrap or in an airtight container in the fridge. Thanks to its rich, creamy texture, it holds up beautifully for up to 4 days and only gets more flavorful as it sits.
Freezing
If you want to save some for later, you can freeze the cheesecake by wrapping it securely in plastic wrap and then foil. Freeze for up to 2 months. When ready to enjoy, thaw in the fridge overnight to maintain the perfect texture of this Pineapple Upside-Down Cheesecake Recipe.
Reheating
This dessert is best enjoyed chilled, so reheating is not recommended. However, if you prefer it slightly warmer, let slices sit at room temperature for 20 minutes before serving to take the chill off without sacrificing creaminess.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple rings work wonderfully and add a vibrant, natural sweetness to your Pineapple Upside-Down Cheesecake Recipe. Just be sure they’re sliced evenly and well-drained to avoid excess moisture.
Why does the recipe use a water bath for baking?
The water bath provides gentle, even heat around the cheesecake, preventing cracking and ensuring a silky, smooth texture that’s essential for a perfect Pineapple Upside-Down Cheesecake Recipe.
Can I make this cheesecake gluten-free?
Yes, simply swap the graham cracker crumbs for gluten-free varieties or use ground nuts like almonds instead. This adjustment keeps the crust delicious while accommodating gluten sensitivities.
How long should I let the cheesecake chill before serving?
For best results, chilling for at least 4 hours is key, but overnight chilling is ideal. It gives the flavors time to develop fully and the texture to set beautifully.
What’s the best way to slice this cheesecake cleanly?
Use a sharp knife dipped in hot water, wiping it clean between cuts for smooth, clean slices that showcase the lovely pineapple topping of this Pineapple Upside-Down Cheesecake Recipe.
Final Thoughts
I can’t recommend this Pineapple Upside-Down Cheesecake Recipe enough if you’re looking to wow your family and friends with a dessert that’s both stunning and soul-satisfying. The balance of caramelized fruit, creamy cheesecake, and crunchy crust is truly something special. So preheat your oven, gather your ingredients, and prepare to treat yourself to a slice of tropical heaven!
Print
Pineapple Upside-Down Cheesecake Recipe
- Prep Time: 40 minutes
- Cook Time: 1 hour 10 minutes
- Total Time: 5 hours 50 minutes
- Yield: 12 servings
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
This Pineapple Upside-Down Cheesecake combines the tropical sweetness of caramelized pineapple rings with a rich, creamy cheesecake layer atop a buttery graham cracker crust. Baked in a water bath for a smooth texture, this dessert is perfect for special occasions or a delightful treat to share.
Ingredients
Crust
- 1 1/2 cups graham cracker crumbs
- 1/4 cup granulated sugar
- 6 tablespoons melted butter
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)
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)
Instructions
- Prepare the pineapple topping: In a small saucepan, melt the butter and brown sugar over medium heat until it starts to bubble and forms a caramel sauce. Pour this mixture into the bottom of a greased 9-inch springform pan. Arrange the pineapple rings neatly over the caramel and place a maraschino cherry in the center of each ring. Set aside.
- Make the crust: In a medium bowl, combine the graham cracker crumbs, granulated sugar, and melted butter until evenly mixed. Press this crumb mixture firmly on top of the pineapple rings in the pan, also pressing slightly up the sides. Place the pan in the refrigerator to chill while preparing the filling.
- Preheat the oven: Set your oven to 325°F (160°C). Wrap the outside of the springform pan with aluminum foil tightly to prevent water from leaking in during baking. Place the springform pan inside a larger baking dish for the water bath.
- Make the cheesecake filling: In a large bowl, beat the softened cream cheese and sugar together until completely smooth and creamy. Mix in the sour cream and vanilla extract thoroughly. Add the eggs one at a time, mixing each just until combined to avoid overbeating. Gently fold in the drained crushed pineapple to maintain texture.
- Assemble and bake: Pour the cheesecake filling over the chilled crust in the springform pan. Carefully place the pan into the prepared larger baking dish and pour hot water into the larger dish until it reaches halfway up the sides of the springform pan. Bake for 60 to 70 minutes, or until the center is mostly set but still slightly jiggly.
- Cool and chill: Remove the springform pan from the water bath and allow the cheesecake to cool completely at room temperature. Once cooled, refrigerate it for at least 4 hours or overnight to firm up and develop flavors.
- Flip and serve: Before serving, run a knife around the edge of the cheesecake to loosen it from the pan. Carefully invert the cheesecake onto a serving platter so that the pineapple rings and cherries are displayed on top. Slice and enjoy your delicious pineapple upside-down cheesecake!
Notes
- Ensure the crushed pineapple used in the filling is well drained to avoid excess moisture.
- Wrapping the springform pan with foil is crucial to prevent water seepage during the water bath baking.
- Allowing the cheesecake to chill overnight improves its texture and flavor.
- Use fresh pineapple rings if possible for a brighter flavor, but canned works well too.
- Be careful when flipping the cheesecake due to its delicate toppings and creamy filling.

