Hey there! So, the other day I was reminiscing about my grandmother’s kitchen (she was a wizard with a whisk). One of the things that takes me right back there is the smell of pineapple upside-down cake. But, I thought, why not make it a bit fancier, but also bite-sized, and boom! Mini Pineapple Upside Down Cheesecakes were born.
Why You’ll Love These Little Treats
Honestly, I whip these up when my sweet tooth is screaming but I don’t want to commit to a whole cake. My family goes absolutely bananas—wait, pineapples?—for these because they’re like little bites of sunshine (and portion control, sort of). Oh, and they’re perfect for those times you want to impress guests without breaking a sweat.
What You’ll Need
- 1 cup crushed graham crackers (sometimes I use digestive biscuits if I’ve got them)
- 1/4 cup melted butter (my grandma swore by unsalted, but I’ve used salted, and it’s fine too)
- 1/2 cup brown sugar
- Canned pineapple slices (fresh is lovely, but canned is just easier, right?)
- 10-12 maraschino cherries
- 16 oz cream cheese, softened (I’ve tried low-fat, but honestly, go full-fat)
- 1/2 cup granulated sugar
- 1 teaspoon vanilla extract (or splash a bit more, I won’t tell)
- 2 large eggs

How to Get These Made
Okay, first up, preheat your oven to 325°F (that’s about 160°C if you’re across the pond). Now, grab a muffin tin and line it with paper liners. You know, this is where I would’ve sneaked a taste of the batter when grandma wasn’t looking.
Start by mixing the graham cracker crumbs with melted butter. Press this crumbly goodness into the bottom of each liner—don’t worry if it’s not perfect! Next, sprinkle each with a bit of brown sugar, pop a pineapple slice on top, and nestle a maraschino cherry right in the center. Cute, huh?
Now, for the cheesecake part: beat the cream cheese until smooth, then add the sugar, vanilla, and eggs. Blend until it’s as smooth as your favorite jazz tune. Spoon this over the pineapple layer, almost to the top (but leave a smidge of space so it doesn’t overflow).
Bake for about 18-20 minutes. They’ll still be a little jiggly in the middle, but that’s okay! Let them cool before popping them in the fridge for at least 2 hours (overnight if you can stand the wait).
Some Notes
I’ve found if you let them sit overnight, the flavors meld together even better. But let’s be honest, resisting is tough.

Try These Variations
Once, I swapped the pineapple for peaches—delicious! But when I tried bananas, it was a bit too mushy. Live and learn.
Equipment Check
No muffin tin? Use a silicone mold or even ramekins if you’re feeling fancy. Just don’t sue me if they stick a bit!

Keeping Them Fresh
Store these in an airtight container in the fridge for up to 5 days, though honestly, in my house, they never last more than a day!
Serving Suggestions
I like to serve these with a dollop of whipped cream on top (because why not?) and a sprinkle of toasted coconut.
A Few Pro Tips
Don’t rush the cooling process—I once did, and ended up with a runny mess. Patience is a virtue, especially here.
Got Questions? Here’s What Folks Ask Me
Can I use fresh pineapple? Sure! Just make sure it’s really ripe for that sweet taste.
What if I don’t like cherries? No problem, leave them out or try candied ginger for a spicy kick!
Do I really need to line the muffin tin? Actually, it helps with removal and cleanup, but if you’re feeling brave, grease it well and go for it!