First off, thank you for stopping by! I am so grateful to have you here, sharing this passion for homemade treats and the joy of bringing smiles to our loved ones through food. Today, I have something truly special for you—Mini Pineapple Upside-Down Cheesecakes. These little beauties are an irresistible combination of classic pineapple upside-down cake and creamy cheesecake. They’re sweet, tangy, rich, and absolutely charming in their mini form. I’m thrilled to walk you through every delicious detail!
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What Are Mini Pineapple Upside-Down Cheesecakes?
Imagine the buttery caramelized pineapple and maraschino cherry goodness of a traditional pineapple upside-down cake, but nestled on top of a velvety cheesecake base, all in a perfectly portioned mini dessert. That’s what we’re talking about today! These are baked in muffin tins, making them ideal for parties, potlucks, or just a sweet indulgence at home.
Why You’ll Love These Mini Cheesecakes:
- Two desserts in one: Cheesecake meets pineapple upside-down cake? Yes, please!
- Perfectly portioned: No slicing needed; just grab and enjoy.
- Crowd-pleasers: The tropical flavor combo is always a hit.
- Freezer-friendly: Make ahead and freeze for those last-minute cravings!
The Flavor Profile:
Think sweet brown sugar caramel mingling with juicy pineapple and a bright cherry pop. All of that is balanced by the smooth, creamy texture of the cheesecake underneath. Each bite is rich, tropical, and decadent—but not overly heavy. The perfect treat to brighten up any occasion!

Benefits of Making Mini Pineapple Upside-Down Cheesecakes
- Portable & shareable: Ideal for gatherings, brunches, or gifting.
- Simple ingredients: Most are pantry staples!
- Elegant presentation: These little cakes look as good as they taste.
- Versatile: Can be made gluten-free with a simple crust swap.
Ingredients You’ll Need
For the Topping:
- 1/2 cup brown sugar (light or dark)
- 1/4 cup unsalted butter, melted
- 12 canned pineapple rings, cut to fit muffin wells
- 12 maraschino cherries
For the Cheesecake Base:
- 12 vanilla wafer cookies (or graham cracker crust alternative)
- 16 oz cream cheese, softened
- 1/2 cup granulated sugar
- 2 large eggs
- 1 tsp vanilla extract
- 1/4 cup sour cream
Tools You’ll Need
- Standard muffin tin (12 wells)
- Hand or stand mixer
- Mixing bowls
- Measuring cups and spoons
- Cooling rack
- Small offset spatula (optional but helpful for releasing the minis)
Optional Additions & Substitutions
- Fruit swap: Try peaches or mango for a twist!
- Gluten-free option: Use gluten-free vanilla wafers or crushed gluten-free cookies for the base.
- Add spice: A dash of cinnamon or nutmeg in the brown sugar mixture adds warmth.
- Liqueur touch: A splash of rum in the cheesecake batter for a tropical kick!

How to Make Mini Pineapple Upside-Down Cheesecakes
Step 1: Prep the Muffin Tin
Grease your muffin tin generously. Preheat the oven to 325°F (163°C).
Step 2: Create the Caramelized Topping
In each muffin well, add about 1 tsp of melted butter and 1 tbsp of brown sugar. Place a cherry in the center and a pineapple piece over it.
Step 3: Make the Cheesecake Batter
Beat the cream cheese and granulated sugar until smooth and fluffy. Add eggs, one at a time, beating well after each. Mix in vanilla and sour cream until just combined.
Step 4: Assemble
Place a vanilla wafer at the bottom of each muffin well on top of the pineapple. Spoon the cheesecake mixture over, filling nearly to the top.
Step 5: Bake
Bake for 20-25 minutes, or until centers are set. Let cool in the pan for about 10 minutes, then run a knife or offset spatula around the edges and invert onto a cooling rack.
Step 6: Chill
Refrigerate for at least 1 hour before serving for best texture.
What to Serve with These Mini Cheesecakes
- Whipped cream with a sprinkle of toasted coconut
- Fresh fruit salad on the side
- Tropical cocktails like piña coladas or mango mojitos
- Coffee or tea for a cozy treat
Tips for Success
- Room temp ingredients: Ensure cream cheese and eggs are at room temperature for a smooth batter.
- Don’t overmix: Mix just until combined to avoid cracks.
- Invert carefully: While still slightly warm for clean removal.
- Chill time: Don’t skip chilling—they’re even better cold!
Storage Instructions
- Refrigerate: Store in an airtight container for up to 5 days.
- Freeze: Individually wrap and freeze for up to 2 months. Thaw in the fridge overnight before serving.
General Information
- Prep Time: 20 minutes
- Cook Time: 25 minutes
- Chill Time: 1 hour
- Total Time: About 1 hour 45 minutes
- Servings: 12 mini cheesecakes

Frequently Asked Questions
Can I use fresh pineapple instead of canned?
Yes! Just make sure to cut it into small enough pieces to fit your muffin wells.
What if I don’t have vanilla wafers?
No worries—use graham crackers, shortbread cookies, or even a homemade crust.
Can I make these ahead of time?
Absolutely! These keep wonderfully in the fridge or freezer, making them perfect for prepping ahead.
How do I prevent cracks?
Be sure not to overbake and allow them to cool gradually before chilling.
In Conclusion
These Mini Pineapple Upside-Down Cheesecakes are anything but boring!! They’re a delightful fusion of two beloved desserts, perfect for any celebration or just because. They come together easily, yet feel like something you’d find at a fancy bakery. I promise, one bite and you’ll be hooked!
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Nutritional Information (Approx. per mini cheesecake)
- Calories: 260
- Fat: 18g
- Carbs: 22g
- Protein: 4g
- Sugar: 16g