Pineapple Right Side Up Cheesecake Recipe
If you’re craving a dessert that perfectly blends the tropical sweetness of pineapple with the creamy indulgence of cheesecake, this Pineapple Right Side Up Cheesecake Recipe is about to become your new favorite. Imagine a luscious, velvety cheesecake crowned with caramelized pineapple rings and just a hint of cinnamon, all resting on a buttery graham cracker crust. It’s a nostalgic twist on the classic upside-down cake but taken to a whole new level of richness and flavor. Whether it’s for a family gathering, a special celebration, or simply to treat yourself, this recipe delivers every time with its delightful balance of tangy, sweet, and creamy textures that melt in your mouth.

Ingredients You’ll Need
This recipe uses simple, everyday ingredients that work harmoniously to create a cheesecake that’s both familiar and exotic. Each component plays a crucial role—from the crumbly buttery crust that forms the perfect base to the smooth, tangy filling and the caramelized pineapple topping that adds a vibrant pop of color and flavor.
- Graham cracker crumbs (1 1/2 cups): Provides a crunchy, sweet foundation with a hint of honey flavor that complements the tropical pineapple.
- Granulated sugar (1/4 cup + 3/4 cup): Balances sweetness in both the crust and filling for a pleasant, not overpowering taste.
- Unsalted butter (1/3 cup melted + 1 tablespoon): Adds richness and helps the crust and pineapple topping caramelize beautifully.
- Cream cheese (3 packages, softened): The creamy heart of the cheesecake, creating that signature smooth and tangy texture.
- Large eggs (3): Bind the cheesecake filling, providing structure and silkiness.
- Vanilla extract (1 teaspoon): Infuses warmth and depth, enhancing the overall flavor without overpowering.
- Sour cream (1/2 cup): Adds a subtle tang and creaminess, lightening the filling’s texture.
- Crushed pineapple (1 can, well-drained, 20 oz): Brings natural sweetness and moisture to the filling for that tropical flair.
- Brown sugar (1/4 cup): Used for caramelizing pineapple rings, contributing to a deliciously sticky and flavorful topping.
- Cinnamon (1/2 teaspoon): Offers a warm spice note to enhance the pineapple topping.
- Pineapple rings and maraschino cherries (optional): For that classic “right side up” look and an extra burst of sweetness and color.
- Whipped cream (optional): Adds light, fluffy contrast when serving—you can’t go wrong with a dollop on top.
How to Make Pineapple Right Side Up Cheesecake Recipe
Step 1: Prepare the Crust
Start by preheating your oven to 325°F (163°C). Combine the graham cracker crumbs, 1/4 cup sugar, and melted butter in a medium bowl. Press this mixture firmly and evenly into the bottom of a 9-inch springform pan. This crust not only provides a sturdy base but also delivers that irresistible buttery crunch that pairs perfectly with the creaminess of the filling. Bake it for 8 minutes, then set aside to cool while you prepare the filling.
Step 2: Make the Cheesecake Filling
In a large mixing bowl, beat the softened cream cheese and 3/4 cup granulated sugar together until you get a smooth and creamy texture without lumps. This step is essential to avoid a grainy cheesecake. Next, add the eggs one at a time, blending thoroughly after each addition. Incorporate the vanilla extract and sour cream until everything is well combined. Finally, gently fold in the well-drained crushed pineapple to add moisture and a tropical twist to your filling.
Step 3: Bake the Cheesecake
Pour the pineapple-infused cream cheese filling over the cooled crust, smoothing out the top with a spatula. Bake in the preheated oven for 50 to 60 minutes. You want the center to be set but still a little jiggly—that perfect cheesecake texture that’s creamy yet firm. When the baking is done, turn off the oven and leave the cheesecake inside with the door slightly open for about an hour. This helps prevent cracks. Then, chill the cheesecake in your refrigerator for at least 4 hours or ideally overnight to let it set beautifully.
Step 4: Caramelize the Pineapple Rings
While the cheesecake chills, melt 1 tablespoon of butter in a small skillet over medium heat. Stir in the brown sugar and cinnamon until the mixture melts and bubbles. Then add the pineapple rings and cook them 2 to 3 minutes per side until they’re beautifully caramelized and golden. Let these cool slightly before arranging them on top of the chilled cheesecake, garnishing with maraschino cherries if you like for that iconic right side up presentation.
How to Serve Pineapple Right Side Up Cheesecake Recipe

Garnishes
Adding whipped cream on top can elevate the Pineapple Right Side Up Cheesecake Recipe to another level of indulgence. It adds a light, airy texture that balances the richness of the cheesecake and enhances the caramelized pineapple’s sweetness and warmth. For an extra pop of color and subtle flavor, sprinkle some toasted coconut flakes or finely chopped nuts.
Side Dishes
This cheesecake pairs wonderfully with fresh fruit salads or a simple scoop of vanilla bean ice cream. The cool, refreshing qualities of these sides complement the cheesecake’s creamy texture and sweet pineapple topping, making the whole dessert experience feel even more vibrant and satisfying.
Creative Ways to Present
Serve individual slices with a drizzle of pineapple syrup or a splash of coconut rum for a boozy tropical flair. You can also use mini springform pans to create personalized mini cheesecakes, each topped with a caramelized pineapple ring and a cherry. The visual appeal will wow your guests and make every slice feel extra special.
Make Ahead and Storage
Storing Leftovers
The Pineapple Right Side Up Cheesecake Recipe keeps beautifully in the refrigerator for up to five days. Store leftovers in an airtight container or cover the cheesecake tightly with plastic wrap to maintain its moisture and prevent it from absorbing other fridge odors.
Freezing
If you want to make this cheesecake ahead of time, it freezes well for up to two months. Wrap the entire cheesecake or individual slices tightly in plastic wrap and then in aluminum foil before freezing. When ready to enjoy, thaw it overnight in the refrigerator to keep that creamy texture intact.
Reheating
While cheesecake is typically enjoyed chilled, if you prefer it at room temperature, simply let it sit out for about 30 minutes before serving. Avoid microwaving as it can cause the texture to change and become overly soft.
FAQs
Can I use fresh pineapple instead of canned crushed pineapple?
Absolutely! Fresh pineapple will add a vibrant, natural flavor but make sure to finely chop and drain it well to avoid excess moisture that could affect the texture of your cheesecake.
What if I don’t have a springform pan?
A springform pan is ideal for cheesecakes because it makes removal easy without damaging the cake, but you can use a regular cake pan lined with parchment paper for easier release—just be very careful when unmolding.
Can I make this cheesecake vegan or dairy-free?
While this traditional Pineapple Right Side Up Cheesecake Recipe relies on cream cheese and butter, there are vegan cream cheese substitutes and plant-based butters you could try, but expect some differences in texture and flavor.
How do I avoid cracks in my cheesecake?
To prevent cracks, bake at a lower temperature, avoid overmixing the batter, and cool the cheesecake gradually in the oven with the door slightly open as described in the recipe.
Can I add a splash of rum or other flavoring?
Yes! Adding a small amount of coconut or pineapple rum to the filling is a fantastic way to boost the tropical vibe without overwhelming the flavors.
Final Thoughts
This Pineapple Right Side Up Cheesecake Recipe is truly a showstopper that brings together the best of tropical flavors and creamy desserts in one unforgettable dish. Whether you’re baking for the holidays, a birthday, or just because you deserve something sweet and special, you’ll love how this cheesecake looks and tastes. So, go ahead and dive in—your next favorite dessert experience awaits!
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Pineapple Right Side Up Cheesecake Recipe
- Total Time: 6 hours 30 minutes
- Yield: 12 servings 1x
- Diet: Vegetarian
Description
This Pineapple Right Side Up Cheesecake combines the rich, creamy texture of classic cheesecake with a tropical twist of caramelized pineapple and warm spices. Featuring a buttery graham cracker crust, smooth cream cheese filling with crushed pineapple, and topped with caramelized pineapple rings and maraschino cherries, this dessert is perfect for any occasion looking for a flavorful, eye-catching finale.
Ingredients
Crust
- 1 1/2 cups graham cracker crumbs
- 1/4 cup granulated sugar
- 1/3 cup unsalted butter, melted
Cheesecake Filling
- 3 packages (8 oz each) cream cheese, softened
- 3/4 cup granulated sugar
- 3 large eggs
- 1 teaspoon vanilla extract
- 1/2 cup sour cream
- 1 can (20 oz) crushed pineapple, well-drained
Topping
- 1/4 cup brown sugar
- 1 tablespoon unsalted butter
- 1/2 teaspoon cinnamon
- Pineapple rings (optional, for topping)
- Maraschino cherries (optional, for topping)
- Whipped cream (optional, for garnish)
Instructions
- Prepare the Crust: Preheat your oven to 325°F (163°C). In a medium bowl, combine the graham cracker crumbs, 1/4 cup granulated sugar, and the melted butter until the mixture is evenly moistened. Press this mixture firmly into the bottom of a 9-inch springform pan to create an even layer. Bake in the preheated oven for 8 minutes, then remove and set aside to cool.
- Make the Cheesecake Filling: In a large mixing bowl, beat the softened cream cheese together with 3/4 cup granulated sugar until smooth and creamy. Add the eggs one at a time, mixing on medium speed and ensuring each egg is fully incorporated before adding the next. Stir in the vanilla extract and sour cream until combined. Gently fold in the well-drained crushed pineapple to evenly distribute it throughout the batter.
- Bake the Cheesecake: Pour the prepared filling over the cooled graham cracker crust, smoothing out the top with a spatula. Place the springform pan on a middle rack in the oven and bake for 50 to 60 minutes, or until the center is mostly set but still slightly jiggly to the touch. Turn off the oven and leave the cheesecake inside with the door slightly open to cool gradually for 1 hour. Then transfer the cheesecake to the refrigerator to chill for at least 4 hours or overnight.
- Caramelize the Pineapple Rings: In a small skillet over medium heat, melt 1 tablespoon of butter. Add the brown sugar and cinnamon, stirring continuously until the mixture melts and starts bubbling. Add the pineapple rings and cook them for 2 to 3 minutes on each side until they become nicely caramelized. Remove from heat and allow to cool slightly.
- Assemble and Serve: Once the cheesecake is fully chilled, carefully arrange the caramelized pineapple rings over the top. Add maraschino cherries in the centers of the pineapple rings if desired. Garnish with whipped cream before serving for an extra touch of indulgence.
Notes
- Ensure the crushed pineapple is thoroughly drained to prevent excess moisture that could affect the cheesecake’s texture.
- For an extra tropical flavor, consider adding a splash of coconut extract to the cheesecake filling.
- Use a springform pan for easy removal of the cheesecake without damaging the edges.
- Allow the cheesecake to chill overnight for best flavor and texture.
- Prep Time: 25 minutes
- Cook Time: 60 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American