As I set out to bake today, a wave of nostalgia washed over me. The moment I flipped the calendar to summer, visions of vibrant gatherings filled my mind, and I couldn’t resist making a Pineapple Upside-Down Cheesecake. This tropical delight melds the creamy comforts of cheesecake with the charming layers of caramelized pineapple, creating a stunning dessert that captures the essence of sun-soaked celebrations. Not only does this recipe deliver a beautiful presentation sure to dazzle your guests, but it also promises delightful flavors that evoke a carefree day on the beach. Whether entertaining or indulging your own sweet tooth, this cheesecake is both a quick prep and an impressive showstopper. Are you ready to uncover the secret to this mouthwatering masterpiece?

Why is Pineapple Upside-Down Cheesecake a Must-Try?
Delightful Fusion: This Pineapple Upside-Down Cheesecake beautifully combines the creamy indulgence of cheesecake with the nostalgic charm of caramelized pineapple, ensuring each bite is a tropical experience.
Visual Showstopper: With its stunning layers of golden pineapple and vibrant cherries, it’s a feast for the eyes that will impress any guest—perfect for summer gatherings!
Easy to Make: Simplicity reigns with this recipe, allowing even novice bakers to shine without hassle.
Versatile Flavors: Feel free to customize by adding coconut or using a different crust, making it your own while still delivering that sought-after tropical vibe.
Crowd Pleaser: This cheesecake serves up to 12, making it an ideal dessert for parties, picnics, or any occasion where dessert lovers gather. Trust me, your friends and family will be asking for seconds!
If you’re looking for more scrumptious delights, don’t forget to check out my Fried Strawberry Cheesecake or try something fun like these Oreo Cheesecake Cookie Cups!
Pineapple Upside-Down Cheesecake Ingredients
• Ready to create this tropical delight? Here’s what you’ll need!
For the Crust
- Graham Cracker Crumbs – Provides structure and a buttery flavor; substitute with gluten-free crumbs if necessary.
- Unsalted Butter – Binds ingredients together for a rich crust; coconut oil can be used for a dairy-free option.
- Brown Sugar – Adds sweetness and depth; white sugar can be used for a milder flavor.
For the Topping
- Pineapple Rings – Essential for that classic look; canned pineapple is more uniform, but fresh works if sautéed first.
- Maraschino Cherries – Adds a lovely pop of color and sweetness; feel free to substitute with fresh cherries for a natural option.
For the Filling
- Cream Cheese – The star of the filling; make sure it’s softened for easy mixing.
- Granulated Sugar – Sweetens the filling and balances the tang of the cream cheese.
- Sour Cream – Offers a tangy flavor and creamy texture; Greek yogurt serves as a great substitute.
- Vanilla Extract – Enhances the overall flavor; always opt for pure vanilla for the best results.
- Eggs – Binds the cheesecake filling; remember, room temperature eggs mix in more easily.
As you gather these ingredients, get ready to embark on a baking adventure that results in a stunning Pineapple Upside-Down Cheesecake!
Step‑by‑Step Instructions for Pineapple Upside-Down Cheesecake
Step 1: Preheat the Oven
Begin by preheating your oven to 325°F (163°C). While it warms up, grease a 9-inch springform pan with non-stick spray or butter to ensure easy removal later. This step is crucial for the Pineapple Upside-Down Cheesecake, as it sets the stage for even baking right from the start.
Step 2: Prepare the Base
Sprinkle a generous layer of brown sugar evenly on the bottom of the prepared springform pan. Next, arrange the pineapple rings on top, allowing them to nestle snugly, and space the maraschino cherries in the center of each ring for a pop of color. Drizzle the melted butter over this fruity layer, letting it soak in for added flavor and moisture.
Step 3: Make the Crust
In a medium bowl, combine the graham cracker crumbs with melted butter until the mixture resembles wet sand. Press this crumb mixture firmly over the pineapple layer in the springform pan, creating an even, compact crust. For best results, place the pan in the freezer for 10-15 minutes to firm up the crust while you prepare the cheesecake filling.
Step 4: Prepare the Filling
In a large mixing bowl, beat the softened cream cheese and granulated sugar together until smooth and creamy, about 2-3 minutes. Gradually add the eggs one at a time, mixing just until incorporated after each addition. Gently fold in the sour cream and vanilla extract until everything is well combined, resulting in a luscious and airy filling for your Pineapple Upside-Down Cheesecake.
Step 5: Assemble the Cheesecake
Carefully pour the cheesecake filling over the crust and pineapple layer in the springform pan, using a spatula to smooth the top. This should create a lovely contrast between the creamy filling and the beautiful pineapple base below. Make sure to tap the pan gently on the counter to eliminate any air bubbles, ensuring a perfect texture.
Step 6: Bake
To bake your Pineapple Upside-Down Cheesecake, set the springform pan in a larger baking dish and fill the dish with hot water until it reaches halfway up the sides of the pan—this creates a water bath for even cooking. Bake in the preheated oven for 60-70 minutes, or until the edges are set and the center is slightly jiggly but not liquid.
Step 7: Cool in the Oven
Once baked, turn off the oven and crack the door open slightly. Allow the cheesecake to cool inside the oven for 1 hour. This gradual cooling helps prevent cracking and stabilizes the texture of your Pineapple Upside-Down Cheesecake as it settles.
Step 8: Chill the Cheesecake
After the hour of cooling, remove the cheesecake from the oven and let it cool at room temperature for about 30 minutes. Then, cover it with plastic wrap and refrigerate for at least 4 hours or overnight. Chilling is essential for the cheesecake to fully set, allowing for perfect slicing.
Step 9: Invert and Serve
When ready to serve, run a knife around the edge of the springform pan to loosen the cheesecake. Release the latch and carefully invert the cheesecake onto a serving plate, ensuring the pineapple topping is on display. With its stunning appearance, your Pineapple Upside-Down Cheesecake is now ready to be sliced and enjoyed!

What to Serve with Pineapple Upside-Down Cheesecake
Creating a delightful meal experience is all about harmony; these pairings bring out the best in your tropical cheesecake!
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Coconut Whipped Cream: The airy lightness and subtle coconut flavor enhance the cheesecake’s tropical vibe, making each bite feel like a mini vacation.
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Fresh Fruit Salad: A medley of seasonal fruits adds a refreshing, vibrant contrast to the creamy richness of the cheesecake; think juicy berries, ripe mango, and zesty citrus.
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Toasted Macadamia Nuts: These nuts provide a delightful crunch and buttery flavor, perfectly complementing the creamy texture of the cheesecake with a touch of nuttiness.
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Pineapple Sorbet: For those hot summer days, a scoop of pineapple sorbet offers a cool, tangy complement to your dessert while keeping the tropical theme alive.
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Mint Tea: A warm cup of mint tea acts as a refreshing after-dinner drink. Its lightness balances the richness of the cheesecake while cleansing the palate.
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Dark Chocolate Drizzle: Elevate your cheesecake by drizzling it with melted dark chocolate; the rich, bittersweet notes create a decadent combination that dessert lovers adore.
Indulge in these delicious pairings, and watch as your Pineapple Upside-Down Cheesecake becomes the star of the gathering!
Make Ahead Options
These Pineapple Upside-Down Cheesecakes are perfect for busy home cooks looking to save time on dessert prep! You can prepare the crust and the pineapple layer up to 24 hours in advance by pressing the graham cracker mixture into the pan and layering the pineapple rings and cherries as instructed. Cover the pan tightly with plastic wrap and refrigerate to maintain freshness. When you’re ready, whip up the cheesecake filling, pour it over the prepped crust, and bake. After baking, allow the cheesecake to cool and chill for at least 4 hours or overnight for a perfect slice. This way, your guests will enjoy a stunning dessert with minimal fuss!
Pineapple Upside-Down Cheesecake Variations
Embrace your creativity and transform this delightful cheesecake into countless variations that ignite your taste buds!
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Gluten-Free: Swap graham cracker crumbs for gluten-free crumbs or almond flour for a delicious gluten-free crust. It ensures everyone can indulge!
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Chocolate Lovers: Use chocolate wafer cookies instead of graham crackers for a rich, cocoa-flavored crust that takes the tropical taste in a fun direction. It’s a chocolatey twist that surprises and delights.
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Dairy-Free: Substitute cream cheese and sour cream with vegan cream cheese and coconut yogurt, creating a dairy-free option that everyone can enjoy without missing out on creaminess.
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Tropical Infusion: Add shredded coconut to both the crust and topping for a true island vacation vibe. You can even sprinkle toasted coconut on top for extra crunch and visual appeal!
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Caramel Drizzle: Enhance the flavor by drizzling homemade caramel sauce on the cheesecake just before serving. This addition provides an extra layer of sweetness and indulgence that elevates every slice.
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Citrus Zest: Incorporate lemon or orange zest into the filling for a zesty fresh note that brightens the cheesecake and complements the pineapple beautifully.
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Fresh Fruit Topping: Replace maraschino cherries with fresh berries or kiwi slices for a refreshing and healthier topping option that adds vibrant color. It provides a delightful contrast to the creamy cheesecake.
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Spice it Up: Sprinkle a touch of cinnamon or nutmeg into the filling for a cozy flavor that brings warmth to this tropical delight. It’s a wonderful surprise that pleasantly complements the pineapple.
As you explore these variations, you may also love to try these delightful recipes like Fried Strawberry Cheesecake or the irresistible Oreo Cheesecake Cookie Cups for more sweet inspirations!
Expert Tips for Pineapple Upside-Down Cheesecake
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Water Bath Necessity: Bake with a water bath to prevent cracks in your cheesecake, ensuring it stays beautifully creamy without unsightly splits.
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Room Temperature Ingredients: Always use room temperature cream cheese and eggs, as this helps to achieve a smoother, lump-free filling for your Pineapple Upside-Down Cheesecake.
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Chill for Ease: Chill the cheesecake overnight for the best texture and easier slicing. It helps set and enhances the flavors beautifully!
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Minimize Soggy Crust: Prevent a soggy crust by freezing it briefly after pressing it into the pan, ensuring a perfect, firm base for your cheesecake.
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Use Canned Pineapple: For consistent texture and caramelization, opt for canned pineapple over fresh. If using fresh, sauté it first until tender.
How to Store and Freeze Pineapple Upside-Down Cheesecake
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Fridge: Keep your Pineapple Upside-Down Cheesecake sealed in an airtight container for up to 5 days to maintain its creamy texture and delicious flavors.
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Freezer: For longer storage, slice the cheesecake and wrap each piece tightly in plastic wrap, then store in a freezer-safe container for up to 3 months.
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Thawing: When you’re ready to enjoy, transfer the frozen slices to the fridge to thaw overnight, allowing the flavors to revive beautifully.
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Reheating: If preferred, you can gently warm individual slices in the microwave for 15-20 seconds to enjoy a cozy, melted experience, bringing back that fresh-out-of-the-oven taste.

Pineapple Upside-Down Cheesecake Recipe FAQs
How do I select ripe pineapple for my cheesecake?
For the most flavorful topping, look for fresh pineapple that feels slightly firm but gives a little when pressed. The skin should be a vibrant golden-yellow with a slight fragrance. Canned pineapple is a great alternative if you’re pressed for time—which I often use for uniformity in flavor!
How should I store leftover Pineapple Upside-Down Cheesecake?
Seal any leftover cheesecake in an airtight container and keep it in the refrigerator for up to 5 days. It’s best served chilled, so just pop it in the fridge and enjoy it later!
Can I freeze Pineapple Upside-Down Cheesecake?
Absolutely! Once the cheesecake is completely cooled and chilled, slice it into individual portions. Wrap each slice tightly in plastic wrap, then place them in a freezer-safe container. Your cheesecake can last up to 3 months in the freezer!
What should I do if my cheesecake cracks during baking?
No worries! A cracked cheesecake can happen even to the best bakers. To prevent this, always bake your cheesecake in a water bath, as it helps to maintain even heat and moisture. If it cracks, don’t fret—just cover it with whipped cream or a layer of fruit topping, and it’ll still taste delightful!
Is this recipe suitable for those with dietary restrictions?
Yes! The Pineapple Upside-Down Cheesecake can be made vegetarian, and you can easily make it gluten-free by using gluten-free graham cracker crumbs. For dairy-free options, try substituting cream cheese with a plant-based alternative and using coconut oil instead of butter. Always remember to check for any allergies if serving to guests!

Pineapple Upside-Down Cheesecake: Tropical Indulgence Awaits
Ingredients
Equipment
Method
- Preheat your oven to 325°F (163°C) and grease a 9-inch springform pan.
- Sprinkle brown sugar evenly on the bottom of the pan, arrange pineapple rings, and place maraschino cherries in the center.
- Drizzle melted butter over the fruit layer.
- In a medium bowl, combine graham cracker crumbs with melted butter until resembling wet sand. Press over the pineapple layer.
- Place the pan in the freezer for 10-15 minutes to firm up the crust.
- Beat cream cheese and granulated sugar until smooth, then gradually add eggs one at a time. Fold in sour cream and vanilla extract.
- Pour cheesecake filling over the crust and pineapple layer, smoothing the top.
- Bake in a water bath for 60-70 minutes until edges are set.
- Cool in the oven for 1 hour, then let it cool at room temperature for 30 minutes before refrigerating for at least 4 hours.
- Run a knife around the edge and invert onto a serving plate to serve.

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