The Pineapple Right Side Up Cheesecake Recipe is an irresistible twist on two classic favorites, combining the tropical sweetness of caramelized pineapple with the rich, creamy texture of cheesecake. This dessert is not only a feast for the eyes with its stunning pineapple-topped presentation but also a deliciously satisfying treat that balances buttery crust, tangy cream cheese, and fruity brightness in every bite. Whether you’re hosting a summer gathering or simply craving something special, this cheesecake will quickly become a beloved favorite in your recipe collection.

Ingredients You’ll Need
Gathering simple ingredients that come together beautifully is the secret to making this Pineapple Right Side Up Cheesecake Recipe stand out. Each ingredient plays a vital role: the buttery crust anchors the dessert, the caramelized pineapple infuses it with tropical flavor, and the creamy filling provides that luscious cheesecake experience we all crave.
- Graham cracker crumbs: This forms a crisp, slightly sweet base that perfectly supports the creamy layers above.
- Granulated sugar: Sweetens both crust and filling, balancing the natural acidity of the pineapple.
- Unsalted butter: Melted butter adds moisture and richness to the crust and helps caramelize the pineapple beautifully.
- Pineapple slices (in juice): The star of the show, providing juicy, tropical flavor and a vibrant look on top.
- Brown sugar: Adds warmth and depth when caramelizing the pineapple slices for that charming right side up effect.
- Cream cheese (softened): Creates the smooth, tangy filling essential for every cheesecake lover’s delight.
- Large eggs: Bind the filling and help it set to that perfect creamy consistency.
- Vanilla extract: Enhances the flavor complexity by adding a rich, comforting aroma.
- Sour cream: Adds moisture and a subtle tang that balances the sweetness of the pineapple and sugar.
- Optional garnishes (maraschino cherries, whipped cream): These add a festive touch and extra flair when serving.
How to Make Pineapple Right Side Up Cheesecake Recipe
Step 1: Prepare the Crust
Start by preheating your oven to 325°F and greasing a 9-inch springform pan—you’ll want to wrap the bottom with foil carefully to avoid any leaks during baking. Combine the graham cracker crumbs, sugar, and melted butter in a bowl, then press this mixture firmly into the bottom and slightly up the sides of your pan. This creates a sturdy and buttery crust that will crisp and complement the creamy layers above. Bake it for about 10 minutes until set and golden, then let it cool while you move on.
Step 2: Caramelize the Pineapple
In a skillet over medium heat, melt 2 tablespoons of butter and stir in the brown sugar until it dissolves into a luscious caramel. Add the drained pineapple slices and cook for a few minutes until they’re lightly caramelized and fragrant. This step not only enhances the pineapple’s sweetness but also develops that beautiful glossy sheen which will look stunning right side up on your cheesecake. Arrange these slices in a single layer over the cooled crust carefully.
Step 3: Mix the Cheesecake Filling
Using a large bowl, beat the softened cream cheese until smooth and silky, ensuring there are no lumps left behind. Add granulated sugar and continue beating until the mixture is light and fluffy—a crucial step for light texture. Incorporate the eggs one at a time, mixing just enough to blend each before adding the next. Finish by folding in the vanilla extract and sour cream gently, creating a luscious and creamy filling that balances tang and sweetness perfectly.
Step 4: Assemble and Bake
Pour the cheesecake filling over the caramelized pineapple layer in the springform pan, smoothing the top with a spatula. For even baking and to prevent cracks, place the pan inside a larger roasting pan and pour about one inch of hot water around it to create a water bath. Bake the cheesecake for 60 to 70 minutes until the edges are lightly set but the center still jiggles just slightly when you gently shake the pan. Turn off the oven, crack the door, and let the cheesecake cool gradually inside for about one hour—this slow cooling helps prevent cracks and ensures a smooth texture.
Step 5: Chill Thoroughly
Once cooled, remove the cheesecake from the oven and refrigerate it for a minimum of 4 hours, though overnight chilling is best. This resting time allows the flavors to meld and the cheesecake to firm up perfectly, making slicing neat and clean every time you serve it.
How to Serve Pineapple Right Side Up Cheesecake Recipe

Garnishes
Adding simple garnishes like bright maraschino cherries or a dollop of whipped cream can turn your Pineapple Right Side Up Cheesecake Recipe from delightful to downright festive. Consider adding extra pineapple slices or juicy chunks on the side for added freshness and texture. These small touches elevate both the appearance and the flavor, making it even more appealing to your guests or family.
Side Dishes
This cheesecake pairs wonderfully with light, fruity side accompaniments such as fresh berry salads or a zesty citrus sorbet. The bright acidity in these sides perfectly contrasts the richness of the cheesecake, creating a balanced dessert experience that’s anything but heavy. For an extra indulgent twist, serve with a drizzle of caramel or a sprinkle of toasted coconut.
Creative Ways to Present
Feel like impressing the crowd? Instead of serving the whole cheesecake, slice it into individual parfaits or mini mason jar desserts layered with crushed graham crackers and pineapple chunks. Another fun idea is to use ring molds for neat slice shapes and top each portion with edible flowers or fresh mint for a sophisticated look that will wow at any occasion.
Make Ahead and Storage
Storing Leftovers
After enjoying your Pineapple Right Side Up Cheesecake Recipe, store any leftovers covered tightly in the refrigerator. Keeping it chilled will preserve the creamy texture and prevent the pineapple topping from drying out. Wrapped properly, it will stay fresh and delicious for up to 4 days, giving you plenty of time to savor every bite.
Freezing
If you want to prepare this cheesecake well in advance or save some for later indulgence, freezing is a great option. Wrap the cheesecake tightly in plastic wrap and then in aluminum foil to protect from freezer burn. When ready to eat, thaw it in the fridge overnight for the best texture. Keep in mind that freeze-thaw cycles may slightly impact the pineapple topping’s texture.
Reheating
Cheesecake is best enjoyed chilled, so reheating is generally not recommended. However, if you prefer a warmer dessert, take the cheesecake out of the refrigerator and let it sit at room temperature for about 20 minutes before serving. This gently loosens the filling without compromising the flavor or texture.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple can bring even more vibrant flavor, but make sure to drain it well and cook it similarly to the canned slices to avoid excess moisture that may affect the crust and filling.
Why do you bake the cheesecake in a water bath?
The water bath provides gentle, even heat that helps prevent cracking and ensures a smooth, creamy texture by avoiding sudden temperature changes during baking.
What can I substitute for sour cream in this recipe?
If you don’t have sour cream, plain Greek yogurt works well as a substitute—it adds similar moisture and mild tang without altering the flavor significantly.
How long does the cheesecake need to chill?
For the best results, chilling the cheesecake for at least 4 hours is essential, but overnight chilling is ideal to let all the flavors meld and the texture fully set.
Can I prepare the cheesecake a day ahead for a party?
Yes, this Pineapple Right Side Up Cheesecake Recipe actually tastes better the next day after all the flavors have had time to develop. It’s a perfect make-ahead dessert for gatherings!
Final Thoughts
If you’re looking to wow friends or family with a dessert that’s both visually stunning and delectably flavorful, give this Pineapple Right Side Up Cheesecake Recipe a try. The beautiful caramelized pineapple topping paired with creamy, rich cheesecake creates a tropical treat that’s perfect any time of year. Baking this dessert is as rewarding as eating it, and once you make it, it’s sure to become a cherished favorite. Happy baking and even happier eating!
Print
Pineapple Right Side Up Cheesecake Recipe
- Prep Time: 30 minutes
- Cook Time: 1 hour 10 minutes
- Total Time: 5 hours
- Yield: 12 servings
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
This Pineapple Right Side Up Cheesecake combines a buttery graham cracker crust with a caramelized pineapple layer topped by a creamy, smooth cheesecake filling. Baked in a water bath for perfect texture and garnished with cherries and whipped cream, it offers a tropical twist on a classic dessert that’s perfect for any occasion.
Ingredients
For the Crust:
- 1 1/2 cups graham cracker crumbs
- 1/4 cup granulated sugar
- 1/2 cup unsalted butter, melted
For the Pineapple Layer:
- 1 can (20 ounces) pineapple slices in juice, drained
- 1/4 cup brown sugar
- 2 tablespoons unsalted butter
For the Cheesecake Filling:
- 3 packages (8 ounces each) cream cheese, softened
- 1 cup granulated sugar
- 3 large eggs
- 1 teaspoon vanilla extract
- 1/2 cup sour cream
For Garnish (optional):
- Maraschino cherries
- Whipped cream
- Extra pineapple slices or chunks
Instructions
- Preheat and Prepare Pan: Preheat your oven to 325°F and grease a 9-inch springform pan. Wrap the bottom of the pan in foil to prevent leaks during baking.
- Make the Crust: In a mixing bowl, combine graham cracker crumbs, granulated sugar, and melted butter. Press this mixture firmly into the bottom and slightly up the sides of the prepared pan. Bake for 10 minutes, then remove and allow to cool.
- Caramelize Pineapple: Heat a skillet over medium heat and melt 2 tablespoons of unsalted butter. Stir in the brown sugar until dissolved and bubbly. Add the drained pineapple slices and cook for 3 to 4 minutes until lightly caramelized. Remove from heat.
- Arrange Pineapple Layer: Place the caramelized pineapple slices in a single layer on top of the baked crust, distributing evenly.
- Prepare Cheesecake Filling: Using a large bowl, beat the softened cream cheese until smooth and creamy. Add granulated sugar and beat until light and fluffy. Incorporate eggs one at a time, mixing after each addition. Add vanilla extract and sour cream, blending until just combined to maintain a smooth texture.
- Assemble Cheesecake: Pour the cheesecake filling over the pineapple layer, smoothing the top with a spatula for an even surface.
- Water Bath Baking: Place the springform pan into a larger roasting pan. Pour about one inch of hot water into the outer pan to create a water bath, which helps bake the cheesecake evenly and prevents cracking.
- Bake: Bake in the preheated oven for 60 to 70 minutes. The cheesecake is done when the edges are set and the center has a slight jiggle.
- Cool in Oven: Turn off the oven and crack the door open. Leave the cheesecake inside to cool slowly for one hour to prevent sudden temperature changes and cracking.
- Chill: Remove the cheesecake from the oven and water bath. Refrigerate for at least 4 hours or overnight to fully set the cheesecake.
- Garnish and Serve: Before serving, optionally garnish the cheesecake with maraschino cherries, whipped cream, or extra pineapple slices or chunks for added flavor and presentation.
Notes
- Ensure pineapple slices are well-drained to avoid soggy crust or filling.
- This cheesecake tastes best after chilling overnight, allowing the flavors to meld and texture to firm up.
- To avoid cracks in the cheesecake, do not overmix the batter and use the water bath method precisely as described.

