If you’re ready to treat yourself to a dessert that’s both nostalgic and refreshingly indulgent, this Pineapple Right Side Up Cheesecake Recipe is your new best friend. Combining the tropical sweetness of pineapple and maraschino cherries with the rich, creamy texture of cheesecake, it beautifully flips the traditional pineapple upside down cake concept into a luscious, elegant dessert that’s perfect for sharing. With its buttery graham cracker crust and silky filling dotted with fruit, every bite feels like a sunny celebration on your taste buds.

Ingredients You’ll Need
Gathering a handful of straightforward but impactful ingredients is the secret to making this cheesecake sing. Each component plays a unique role in creating the perfect balance of texture, flavor, and visual appeal.
- Graham cracker crumbs: These form the crunchy, buttery base that anchors the cheesecake beautifully.
- Brown sugar: Adds a subtle molasses note enhancing the crust’s caramel-like flavor.
- Sugar: Essential for sweetening both crust and filling to just the right level.
- Melted butter: Binds the crust crumbs and peppers richness throughout.
- Cream cheese: The superstar for that signature creamy cheesecake texture and tang.
- Sour cream: Adds a slight tartness and makes the texture heavenly smooth.
- Heavy cream: Elevates creaminess and richness with just a splash.
- Vanilla extract: Brings warmth and depth, harmonizing all flavors.
- Cornstarch: A little secret that helps stabilize the filling for a perfect slice.
- Eggs: The natural binder that creates structure.
- Maraschino cherries: Chopped in half, offering bursts of vibrant color and sweetness inside.
- Canned pineapple chunks: The star fruit, tender and juicy, delivering that tropical brightness throughout.
How to Make Pineapple Right Side Up Cheesecake Recipe
Step 1: Prepare Your Oven and Pan
Start by preheating your oven to 300°F (149°C). Using a 6×3-inch removable bottom pan is key – it allows you to easily lift out the cheesecake without any damage, ensuring a flawless presentation.
Step 2: Make the Graham Cracker Crust
Mix the graham cracker crumbs with brown sugar and granulated sugar, then slowly add melted butter until the mixture holds together nicely. Press this into the bottom of your pan evenly. Bake the crust for 10 to 12 minutes to give it a golden, toasted depth that contrasts beautifully with the creamy filling. Let it cool completely before the next step.
Step 3: Whip Up the Cheesecake Filling
Beat the cream cheese until luxuriously creamy and smooth. Add sour cream, heavy cream, vanilla extract, sugar, and cornstarch, mixing well to incorporate each for that classic cheesecake richness and stability. Gently fold in the eggs – room temperature helps everything blend seamlessly – and finally, carefully fold in your halved maraschino cherries and pineapple chunks so every slice is bursting with fruit.
Step 4: Bake with Care
Pour your peachy, fruity filling into the cooled graham cracker crust. Bake at 300°F for 12 minutes; then lower the temperature to 225°F and continue baking for another 95 minutes. This slow bake gives you a dense but delicate texture. Allow the cheesecake to cool in the oven with the door slightly ajar – this gradual temperature change prevents cracks and ensures smoothness.
Step 5: Chill Overnight
Once cool, refrigerate your Pineapple Right Side Up Cheesecake Recipe overnight. This resting period is crucial to let the flavors meld and the texture to firm up into that classic, sliceable cheesecake perfection.
How to Serve Pineapple Right Side Up Cheesecake Recipe

Garnishes
Enhance your dessert’s tropical vibe by topping it with a swirl of freshly whipped cream, extra pineapple slices, and cherries. These not only elevate the look but add fresh, juicy notes with every bite.
Side Dishes
Pair with a light fruit salad or a scoop of coconut ice cream to complement the cheesecake’s creamy sweetness with contrasting textures and tropical flavors. A drizzle of caramel sauce can also be a decadent finishing touch.
Creative Ways to Present
Try serving this cheesecake on a rustic wooden board with tropical leaves for a fun, summery display. Individual mini cheesecakes or cheesecake parfaits layered with crushed graham crackers, pineapple, and cherries can also be delightful twists for parties.
Make Ahead and Storage
Storing Leftovers
Keep any leftover Pineapple Right Side Up Cheesecake Recipe in an airtight container in the refrigerator. It will stay fresh and delicious for up to 4 days, maintaining its creamy texture and vibrant fruit flavors.
Freezing
For longer storage, wrap the cheesecake tightly in plastic wrap and aluminum foil before freezing. Frozen cheesecake keeps well for up to 2 months. Thaw in the fridge overnight before serving to preserve the best taste and texture.
Reheating
Cheesecake is best enjoyed chilled, so rather than reheating, bring it to room temperature for about 15 minutes before slicing. This allows the flavors to soften and the texture to be perfectly smooth.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple can add a bright, juicy freshness, but be sure to drain excess juice well to avoid a soggy crust or filling.
Why do I need to cool the cheesecake in the oven?
Cooling slowly in the oven prevents the sudden temperature shock that can cause cracks, helping the cheesecake maintain its smooth, beautiful surface.
What does the cornstarch do in the filling?
Cornstarch acts as a stabilizer, helping the cheesecake set firmly and hold its shape when sliced, so you get neat, clean pieces.
Can I make this cheesecake gluten-free?
Yes! Simply swap the graham cracker crumbs for gluten-free alternatives, and ensure your other ingredients are gluten-free certified.
Is it okay if the cheesecake jiggles a little when done baking?
Yes, a slight jiggle in the center is perfect. The cheesecake will firm up as it cools and chills, so don’t worry if it looks a bit soft right out of the oven.
Final Thoughts
There is something so wonderfully satisfying about making and sharing this Pineapple Right Side Up Cheesecake Recipe. It’s a crowd-pleaser that feels both classic and unique, refreshing and decadently rich all at once. Don’t hesitate—grab these simple ingredients and put a tropical twist on your next dessert night. Your friends and family will thank you for this sunny slice of heaven!
Print
Pineapple Right Side Up Cheesecake Recipe
- Prep Time: 30 minutes
- Cook Time: 1 hour 47 minutes
- Total Time: 24 hours 17 minutes (including chilling time)
- Yield: 8 servings
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
This Pineapple Right Side Up Cheesecake is a delightful twist on the classic dessert, featuring a graham cracker crust topped with juicy pineapple chunks and maraschino cherries mixed into a creamy, smooth cheesecake filling. Slow baked to perfection, it offers a rich yet light texture and a beautiful presentation that’s perfect for any occasion.
Ingredients
Crust
- 1 ¼ cups graham cracker crumbs
- 46 grams brown sugar
- 6–7 tablespoons melted butter (add slowly, may not need all)
Filling
- 16 ounces cream cheese, room temperature
- 80 grams sour cream, room temperature
- 1 tablespoon heavy cream, room temperature
- 1 tablespoon vanilla extract
- 140 grams granulated sugar
- 2 tablespoons cornstarch
- 2 eggs, room temperature
- 25 maraschino cherries, cut in half
- 4 slices canned pineapple, cut into chunks
Instructions
- Preheat and Prepare Pan: Preheat your oven to 300°F (149°C) and prepare a 6×3-inch removable bottom pan by greasing it lightly or lining it to prevent sticking.
- Make and Bake Crust: Combine graham cracker crumbs, brown sugar, and melted butter, mixing until the crumbs are evenly moistened. Press this mixture firmly into the bottom of your pan. Bake the crust for 10-12 minutes until set and fragrant, then remove and let it cool completely.
- Prepare Cheesecake Filling: Beat the cream cheese until smooth and creamy. Add sour cream, heavy cream, vanilla extract, granulated sugar, and cornstarch, mixing until the batter is silky and free of lumps.
- Add Eggs and Fruit: Gently incorporate the eggs one at a time to avoid overmixing. Fold in the halved maraschino cherries and pineapple chunks evenly into the batter to distribute fruit flavor throughout.
- Assemble and Bake: Pour the cheesecake filling over the cooled crust. Bake initially at 300°F for 12 minutes, then reduce the oven temperature to 225°F and continue baking for 95 minutes. This slow baking process ensures a creamy texture without cracks. Once done, let the cheesecake cool inside the oven to prevent cracking, then refrigerate it overnight to set completely.
- Garnish and Serve: Before serving, garnish the cheesecake with whipped cream, pineapple slices, and maraschino cherries for an attractive finish and extra flavor.
Notes
- Make sure all dairy ingredients are at room temperature to avoid lumps in the batter.
- Cooling the cheesecake slowly in the oven helps prevent cracks on the surface.
- Using a removable bottom pan makes it easier to remove the cheesecake without damage.
- Chilling overnight enhances the flavor and texture, so plan ahead.
- You can substitute fresh pineapple if preferred, but canned pineapple provides consistent sweetness and texture.

