The aroma of caramelized pineapple wafting through the air instantly transports me to sun-kissed shores, savoring every bite of this Tropical Pineapple Upside-Down Cheesecake. Combining velvety cream cheese with the vibrant sweetness of golden pineapple, it creates a dessert that dazzles at first sight and delivers unforgettable flavor. What I adore most is how effortlessly it elevates gatherings, making every occasion feel special, all while being surprisingly simple to whip up. You’ll find its decadent creaminess paired with a buttery graham cracker crust will steal the spotlight, captivating friends and family alike. Can you resist the allure of this tropical twist on a classic? Let’s dive into the delightful world of baking!

Why is this cheesecake so irresistible?
Tropical Bliss: This Pineapple Upside-Down Cheesecake perfectly marries luscious creaminess with caramelized pineapple’s sweet, tangy notes.
Effortless Elegance: Impressing guests has never been simpler! With straightforward steps and accessible ingredients, this dessert feels gourmet without the fuss.
Crowd-Pleaser: It’s the ideal showstopper for parties, family gatherings, or date nights, ensuring your dessert table shines.
Versatile Delight: Feel free to swap in other fruits or add a splash of rum for a unique twist. And if there’s leftover cheesecake, it’s a flavorful treat for days!
Treat yourself to this delightful twist on a classic and brighten your day. For more delightful cheesecake options, check out my Cookie Butter Cheesecake Cups or the Apple Cheesecake Bars.
Pineapple Upside-Down Cheesecake Ingredients
• Here’s everything you need to create this tropical delight!
For the Crust
- Graham Cracker Crumbs – Offers a crunchy base that complements the creamy cheesecake. Swap with digestive biscuits for a different flavor.
- Unsalted Butter (1/4 cup, melted) – Binds the crust, adding richness; coconut oil works well for a dairy-free option.
- Brown Sugar (1/2 cup) – Sweetens and enhances caramelization of the pineapple; granulated sugar can be used, but it will alter the flavor slightly.
For the Topping
- Pineapple Rings (6 to 8, canned or fresh) – Key for that tropical sweetness and flair; canned ensures even caramelization, while fresh should be sautéed thinly for best results.
- Maraschino Cherries (6 to 8) – Adds a burst of color and sweetness; optional but highly recommended for garnish.
For the Cheesecake Filling
- Cream Cheese (24 ounces, softened) – Provides the creamy base; vegan cream cheese is a great substitute.
- Granulated Sugar (3/4 cup) – Sweetens the filling; alternative sweeteners can also be considered if desired.
- Sour Cream (1/2 cup) – Contributes creaminess and a slight tang; Greek yogurt can be a healthier substitute.
- Vanilla Extract (1 teaspoon) – Enhances overall flavor; consider using vanilla bean paste for a deeper taste.
- Eggs (3 large) – Essential for structure and setting the filling; flax eggs are a good vegan alternative.
Step‑by‑Step Instructions for Pineapple Upside-Down Cheesecake
Step 1: Preheat the Oven and Prepare the Pan
Begin by preheating your oven to 325°F (163°C). Grease a 9-inch springform pan with butter or cooking spray to ensure easy release later. This preparatory step will set the stage for your delicious Pineapple Upside-Down Cheesecake, ensuring its crust is crisp and your layering stays intact.
Step 2: Create the Topping Layer
Sprinkle ½ cup of brown sugar evenly at the bottom of the greased pan. Next, carefully arrange 6 to 8 pineapple rings over the sugar, placing a maraschino cherry in the center of each ring for a pop of color. Drizzle melted butter over the pineapples, allowing the sugars to caramelize beautifully during baking, which enhances the tropical flavors.
Step 3: Prepare the Crust
In a mixing bowl, combine graham cracker crumbs with ¼ cup melted butter until the mixture resembles wet sand. Press this crumb mixture firmly over the pineapple layer, ensuring it’s evenly distributed for a solid base. To help it set, place the crust in the freezer for about 10 to 15 minutes while you prepare the creamy filling.
Step 4: Mix the Cheesecake Filling
In a large mixing bowl, beat 24 ounces of softened cream cheese and ¾ cup granulated sugar until smooth and creamy, about 3-4 minutes. Add in 3 large eggs, one at a time, mixing well after each addition. Then, blend in ½ cup sour cream and 1 teaspoon vanilla extract, ensuring everything is fully incorporated for a rich filling.
Step 5: Assemble the Cheesecake
Carefully pour the cheesecake filling over the chilled crust and pineapple topping, using a spatula to smooth the surface. This step ensures every slice of your Pineapple Upside-Down Cheesecake is creamy and delightful, with a balanced layer of fruit and crust that complements the rich filling beautifully.
Step 6: Bake in a Water Bath
To create a gentle baking environment, place the springform pan into a larger baking dish filled with hot water, about halfway up the sides of the pan. Bake in the preheated oven for 60 to 70 minutes, until the edges are set and the center slightly jiggles when shaken. This technique prevents cracks and keeps your cheesecake silky smooth.
Step 7: Cool Gradually
Once baked, turn off the oven and leave the door slightly ajar. Allow the cheesecake to cool in the oven for about 1 hour; this gradual cooling process helps prevent any sudden temperature changes that could crack the surface. You’ll see it gradually setting and stabilizing, ensuring the perfect texture.
Step 8: Chill in the Refrigerator
After it has cooled, refrigerate the cheesecake for at least 4 hours or, for best results, overnight. Chilling enhances the flavors, solidifies the texture, and makes slicing easier. Allowing the Pineapple Upside-Down Cheesecake to rest will reward you with a slice that’s perfect and firm.
Step 9: Release and Serve
Before serving, run a knife around the edge of the springform pan to loosen the cheesecake. Carefully release the springform base and invert the cheesecake onto a serving plate. The stunning pineapple design will greet you, ready to impress your family and friends with its tropical flair.

Make Ahead Options
These Pineapple Upside-Down Cheesecake creations are perfect for meal prep, helping you save time in your busy week! You can prepare the crust and the pineapple topping up to 24 hours in advance. Simply make the crust and layer it with brown sugar, pineapple rings, and cherries, then cover tightly with plastic wrap and refrigerate. For the cheesecake filling, mix it just before baking for the best texture, but if you need to, you can beat the filling ingredients and store it in the fridge for up to 3 days. When ready to serve, pour the cheesecake filling over your prepared base and bake as directed—your dessert will taste just as delicious as if it were made fresh!
How to Store and Freeze Pineapple Upside-Down Cheesecake
Fridge: Store leftover cheesecake tightly covered in the refrigerator for up to 5 days. The flavors deepen as it sits, making each slice even more delicious!
Freezer: For longer storage, wrap individual slices in plastic wrap, then place them in an airtight container or a freezer bag. They can be frozen for up to 3 months.
Thawing: When you’re ready to enjoy, thaw slices in the fridge overnight. This gentle method preserves the creamy texture of your Pineapple Upside-Down Cheesecake.
Reheating: If you prefer it slightly warm, gently reheat individual slices in the microwave for about 10-15 seconds, just until the filling softens, but take care not to overheat!
What to Serve with Pineapple Upside-Down Cheesecake
Elevate your dessert experience with perfect pairings that bring out the cheesecake’s tropical sweetness and creamy richness.
- Whipped Cream: A dollop of fresh whipped cream adds lightness and balances the richness, enhancing every bite of your cheesecake.
- Tropical Fruit Salad: A mix of fresh mango, kiwi, and berries provides vibrant flavors and textures, creating a refreshing contrast to the cheesecake.
- Coconut Flan: The smooth, creamy texture of flan beautifully complements the cheesecake, while adding a subtle coconut flavor for a tropical touch.
- Vanilla Ice Cream: The cold, creamy ice cream serves as a delightful contrast to the warm caramelized pineapple, making each mouthful a blissful indulgence.
- Pineapple Juice Cocktail: Serve a refreshing cocktail with pineapple juice and coconut rum for a tropical drink that echoes the flavors of the cheesecake, perfect for celebrations.
Pairing homemade treats with your Pineapple Upside-Down Cheesecake can transform your gathering into an unforgettable culinary adventure, embracing the joy of sharing delicious moments with loved ones.
Pineapple Upside-Down Cheesecake Variations
Feel free to explore these delightful twists and substitutions that will make your Pineapple Upside-Down Cheesecake even more extraordinary!
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Fruit Swaps: Substitute pineapple with other fruits like peaches or pears for a delicious variation that brings a new flavor profile. This simple change keeps the essence of the dessert while inviting seasonal sweetness.
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Rum Infusion: Add a tablespoon of rum to the cheesecake filling for an adult twist that enhances the tropical flair. Just imagine the cozy warmth mingling with the creamy cheesecake—pure bliss!
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Toasted Coconut Topping: Sprinkle some toasted coconut flakes over the cheesecake before serving for an added crunch and a burst of tropical aroma. This little touch elevates your dessert visually and flavor-wise.
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Nutty Crust: Swap in finely crushed macadamia nuts or walnuts mixed with the graham cracker crumbs for a delightful nutty crunch that complements the creamy filling perfectly.
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Vegan Option: Use plant-based cream cheese and flax eggs to create a vegan version without sacrificing any of the delicious flavors. Everyone can enjoy a slice of this tropical delight!
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Choco-Pineapple Delight: Drizzle melted dark chocolate over the cheesecake before serving for a decadent chocolate-pineapple combo that will send your taste buds into overdrive.
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Lemon Zest: Stir in a teaspoon of fresh lemon zest into the cheesecake filling for a zesty brightness that balances the tropical sweetness nicely. It’s a refreshing twist that adds complexity!
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Mini Cheesecakes: Create individual mini cheesecakes in muffin tins for delightful portion control and easy serving at gatherings. Kids and adults alike will love having their very own treat!
These variations will not only breathe new life into your Pineapple Upside-Down Cheesecake but will also make every baking experience a fun adventure! If you’re looking for more cheesecake inspiration, check out my Brown Butter Cheesecake or try the classic Sugar Cookie Cheesecake.
Expert Tips for Pineapple Upside-Down Cheesecake
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Water Bath Essential: Using a water bath helps keep the cheesecake moist and prevents cracks. Don’t skip this step for a smooth finish!
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Crust Prep: Always freeze the crust before adding the filling to avoid a soggy base. This ensures a delightful crunch with each bite of your cheesecake.
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Chill Time Matters: For the best flavor and texture, refrigerate your Pineapple Upside-Down Cheesecake overnight. Patience truly makes perfect!
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Slicing Trick: When serving, use a sharp knife dipped in hot water for clean cuts. This preserves the beautiful layers of your cheesecake.
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Fruit Variations: Feel free to experiment with different fruits like peaches or pears for a unique twist on the classic pineapple topping!

Pineapple Upside-Down Cheesecake Recipe FAQs
How do I choose ripe pineapple for this recipe?
Absolutely! If you’re opting for fresh pineapple, look for one that is slightly golden and fragrant at the crown. A ripe pineapple will have a firm body but yield slightly when pressed. Avoid any with dark spots or a sour smell, which could indicate over-ripeness.
How should I store leftover Pineapple Upside-Down Cheesecake?
Very! To keep your cheesecake fresh, cover it tightly and store it in the refrigerator for up to 5 days. It will actually improve in flavor over time, making leftovers a delicious treat! If you want to save it longer, consider freezing slices for up to 3 months.
What’s the best way to freeze Pineapple Upside-Down Cheesecake?
Sure thing! To freeze, wrap individual slices in plastic wrap, ensuring they are airtight. Then place them in a freezer-safe bag or container. Label with the date so you’ll know when they were made. When you’re ready to enjoy, simply thaw them overnight in the fridge.
My cheesecake cracked while baking. What went wrong?
Oh no! Cracks can occur due to rapid temperature changes. To avoid this, always use a water bath when baking, which creates a gentle cooking environment. Also, remember to gradually cool your cheesecake in the oven after baking, as this helps it set without cracking.
Can I use alternative ingredients for dietary restrictions?
Certainly! Many substitutions work well, such as using vegan cream cheese and flax eggs to make it dairy-free and egg-free. Sour cream can be swapped with Greek yogurt for a healthier option. Be mindful of sugar alternatives if you’re watching your sweetness levels.
Is this cheesecake suitable for pets?
No, this cheesecake isn’t suitable for pets, as it contains ingredients like sugar and cream cheese, which can be harmful to them. It’s best enjoyed as a human treat, so keep it safely away from your furry friends!

Pineapple Upside-Down Cheesecake That's a Tropical Dream
Ingredients
Equipment
Method
- Preheat your oven to 325°F (163°C). Grease a 9-inch springform pan with butter or cooking spray.
- Sprinkle ½ cup of brown sugar evenly at the bottom of the greased pan. Arrange 6 to 8 pineapple rings over the sugar and place a maraschino cherry in the center of each ring.
- Combine graham cracker crumbs with ¼ cup melted butter until the mixture resembles wet sand. Press this crust mixture firmly over the pineapple layer and freeze for 10 to 15 minutes.
- Beat 24 ounces of softened cream cheese and ¾ cup granulated sugar until smooth. Add in 3 large eggs, one at a time, mixing well. Blend in ½ cup sour cream and 1 teaspoon vanilla extract.
- Pour the cheesecake filling over the chilled crust and pineapple topping, smoothing the surface with a spatula.
- Place the springform pan into a larger baking dish filled with hot water, about halfway up the sides of the pan. Bake for 60 to 70 minutes.
- Turn off the oven and leave the door slightly ajar. Allow the cheesecake to cool in the oven for about 1 hour.
- Refrigerate the cheesecake for at least 4 hours or overnight for the best results.
- Run a knife around the edge of the springform pan to loosen the cheesecake. Carefully release the springform base and invert onto a serving plate.

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