Mini Pineapple Upside-Down Cheesecakes: Tropical Sweetness in Every Bite

Why You’ll Love This Recipe

If you love the nostalgic flavor of pineapple upside-down cake and the creamy indulgence of cheesecake, these Mini Pineapple Upside-Down Cheesecakes bring the best of both worlds together. Each bite combines the buttery caramelized pineapple topping with smooth, tangy cheesecake and a soft, cookie-like crust — a perfect balance of tropical sweetness and creamy decadence. They’re beautiful enough for special occasions yet simple enough for everyday indulgence. When I made these, I used crushed pineapple and a maraschino cherry in each cup — the presentation was stunning, and the flavor? Pure sunshine. Whether served at parties, holidays, or a summer gathering, these bite-sized treats always steal the show.

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Ingredients

(Tip: You can find the complete list of ingredients and their measurements in the recipe card below.)

Crushed pineapple: The tropical star of the show — canned crushed pineapple works perfectly, adding juicy sweetness to each mini cheesecake.

Brown sugar: Mixed with butter to form that classic caramelized pineapple topping.

Butter: Use unsalted butter, melted, to create the buttery caramel base and to mix into the crust.

Maraschino cherries: Bright red cherries add color and a touch of old-fashioned charm to every cheesecake.

Graham cracker crumbs: Form the base of the crust — buttery and slightly crunchy, balancing the creamy filling.

Cream cheese: The heart of the cheesecake — use full-fat cream cheese, softened, for the creamiest texture.

Sugar: Sweetens the filling without overpowering the natural tartness of the cream cheese.

Egg: Helps the cheesecakes set perfectly while keeping them soft and smooth.

Vanilla extract: Adds warmth and depth to the cheesecake layer.

Salt: Just a pinch enhances all the flavors and prevents the dessert from being too sweet.

Pineapple juice: A splash in the filling ties the whole dessert together with a subtle tropical note.

I once tried adding a little rum extract to the batter for a piña colada-inspired version — it was a fun, tropical twist that guests loved!

Directions

Preheat your oven to 325°F (160°C). Line a 12-cup muffin tin with paper liners and lightly spray them with nonstick spray.

Start by making the pineapple topping. In a small bowl, mix melted butter with brown sugar. Spoon about 1 teaspoon of the mixture into the bottom of each muffin liner. Add a teaspoon of crushed pineapple over the brown sugar mixture, then place half a maraschino cherry in the center.

Next, prepare the crust. In another bowl, combine graham cracker crumbs with melted butter until evenly moistened. Add about 1 tablespoon of the crumb mixture on top of each pineapple layer and press it down gently with the back of a spoon.

Now, make the cheesecake filling. Beat cream cheese and sugar together until smooth and creamy. Add the egg, vanilla extract, and pineapple juice, mixing until well combined and silky. Divide the cheesecake mixture evenly among the muffin cups, filling almost to the top.

Bake for 18–20 minutes, or until the centers are set but slightly jiggly. Let cool in the pan for 15 minutes, then transfer to a wire rack to cool completely. Chill in the refrigerator for at least 2 hours.

Before serving, gently peel off the liners and invert each cheesecake so the pineapple-cherry topping faces up. The buttery caramel glaze will glisten beautifully, making them as stunning as they are delicious.

Essential Equipment

Must-Have Tools to Get Rolling

Here’s what you’ll want to have on hand:

Silicone Spatula – Durable, heat-resistant silicone spatula perfect for mixing, scraping, and spreading. Gentle on non-stick cookware and easy to clean.

Large pot – You’ll need this to boil the whole cabbage head and soften the leaves.

large bowl –Spacious, durable large bowl ideal for mixing, serving, or food preparation. Made from sturdy material and easy to clean.

Sharp knife – For coring the cabbage and slicing out the thick stem in each leaf. A paring knife works best.

Mixing bowl – A big bowl makes it easier to combine your meat and rice filling evenly.

Cutting board – For prepping cabbage leaves and rolling them like a pro.

9×13-inch baking dish – Ideal size to fit your rolled cabbage leaves snugly and prevent them from unraveling.

knife – A sharp, durable kitchen knife perfect for slicing, chopping, and dicing with ease.

Servings and timing

Makes 12 mini cheesecakes
Prep time: 20 minutes
Cooking time: 20 minutes
Chilling time: 2 hours
Total time: 2 hours 40 minutes

Storage/reheating

Store the cheesecakes in an airtight container in the refrigerator for up to 5 days. For longer storage, freeze them for up to 2 months. To serve from frozen, thaw overnight in the fridge. These cheesecakes are best enjoyed chilled — the flavor intensifies, and the texture becomes perfectly creamy.

Variations and Customizations

Piña Colada Cheesecakes

Add rum extract or a splash of coconut milk to the cheesecake batter for a tropical island twist.

Coconut Crust

Mix shredded coconut into the graham cracker crumbs for extra texture and flavor.

Gluten-Free Option

Use gluten-free graham crackers or almond flour for the crust.

White Chocolate Drizzle

Drizzle melted white chocolate over the chilled cheesecakes for an elegant finish.

Citrus Burst

Add lemon or lime zest to the cheesecake batter for a bright, zesty twist.

Caramel Pineapple

Top the finished cheesecakes with a drizzle of salted caramel sauce for added richness.

No-Bake Version

Use a no-bake cheesecake filling and chill overnight instead of baking for a quicker option.

Tropical Fruit Mix

Add finely diced mango or papaya with the pineapple for extra color and sweetness.

Mini Cheesecake Bars

Press the crust and filling into an 8×8-inch pan, bake, chill, and cut into bars.

Chocolate Crust Twist

Use chocolate cookie crumbs instead of graham crackers for a fun flavor contrast.

FAQs

Can I use fresh pineapple?

Yes, just finely chop it and drain well to avoid excess moisture.

Can I make these without liners?

You can, but liners make removing and inverting them much easier.

What’s the best way to prevent cracks?

Don’t overmix the batter and let the cheesecakes cool gradually.

Can I use light cream cheese?

Yes, but full-fat cream cheese gives the best texture.

Can I make them ahead of time?

Absolutely — they taste even better after chilling overnight.

Can I skip the cherries?

Of course — you can use just pineapple or add a small piece of strawberry instead.

Can I make a large version instead of minis?

Yes, bake in a 9-inch springform pan for 45–50 minutes and adjust the topping accordingly.

What’s the best topping for serving?

A dollop of whipped cream or toasted coconut flakes looks and tastes wonderful.

How do I keep the pineapple from making the crust soggy?

Drain the crushed pineapple well and blot with paper towels before layering.

Can I make them vegan?

Yes, use vegan cream cheese, coconut oil for the crust, and plant-based butter substitutes.

Conclusion

Mini Pineapple Upside-Down Cheesecakes are bite-sized perfection — creamy, buttery, and bursting with tropical flavor. The caramelized pineapple topping paired with silky cheesecake creates a dessert that’s both nostalgic and sophisticated. Whether you serve them for the holidays, summer gatherings, or casual family dinners, these mini cheesecakes always deliver sunshine in every bite. Simple to make and stunning to serve, they’re proof that the best desserts come in small, irresistible packages.

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