If you’re looking to wow your friends or family with something that feels both classic and a bit unexpected, this Pineapple Upside-Down Cheesecake Recipe is a real winner. It combines the gooey, caramelized charm of a traditional pineapple upside-down cake with the rich, creamy indulgence of cheesecake. I love how the pineapple rings create this beautiful, golden crown on top, making every slice look as stunning as it tastes.

Whenever I bring this to a gathering or make it for a special dessert night, it always gets compliments and second helpings. The sweetness of brown sugar and the tang of cream cheese balance perfectly, and the maraschino cherries add those little pops of color and flavor that you didn’t know you needed. I’m excited to share my favorite Pineapple Upside-Down Cheesecake Recipe with you because it’s straightforward and truly special.

Ingredients You’ll Need

Each ingredient in this Pineapple Upside-Down Cheesecake Recipe plays a key role in creating the perfect texture and flavor harmony. I always recommend picking quality cream cheese and ripe pineapple for the best outcome. Here’s a quick rundown of what you’ll want to gather:

Graham cracker crumbs: These create a buttery, crunchy crust that contrasts nicely with the smooth cheesecake.
Unsalted butter: Melted for mixing into the crust and drizzling over the pineapple.
Brown sugar: For that classic caramel flavor under the pineapple rings.
Pineapple rings (canned or fresh): Canned works best for consistent slices and caramelization, but fresh adds a juicy zing.
Maraschino cherries: Adds a pop of color and a sweet bite in the center of each pineapple ring.
Cream cheese: The star of the cheesecake; make sure it’s softened to avoid lumps.
Granulated sugar: Sweetens the cheesecake filling evenly.
Sour cream: Adds moisture and tang that keeps the cheesecake from being too dense.
Vanilla extract: Just a little for warmth and depth of flavor.
Eggs: These bind the filling and help set the cheesecake.

Variations

I love tweaking this Pineapple Upside-Down Cheesecake Recipe depending on the occasion and what I have on hand. Feel free to make it your own! It’s great for experimenting with flavors or adapting to dietary needs.

Use fresh pineapple and grill it: I tried this once for a summer BBQ and the smoky grilled pineapple was a game changer.
Swap sour cream for Greek yogurt: For a slightly tangier, lighter version that still keeps the creamy texture.
Make it gluten-free: Use gluten-free graham cracker crumbs to keep the crust safe for gluten-sensitive guests.
Add toasted coconut: Sprinkle some on top after flipping for a tropical flair and crunchy texture.
Mini versions: Use muffin tins instead of a springform pan to make cute individual cheesecakes perfect for parties.

How to Make Pineapple Upside-Down Cheesecake Recipe

Step 1: Prepare the fruit and caramel base

Start by preheating your oven to 325°F and greasing your springform pan well. Sprinkle the brown sugar evenly across the bottom, then arrange your pineapple rings neatly on top. Don’t forget to place a maraschino cherry in the center of each ring—this little detail makes it look wonderful when flipped. Drizzle the melted butter over the fruit and sugar, which will melt and caramelize during baking, giving that signature glossy top.

Step 2: Make and set the crust

Mix the graham cracker crumbs and melted butter until the mixture resembles wet sand. Press this crumbly crust firmly over the pineapple layer—not on top, but right over it—so you get that crunchy, buttery crust nestled under the cheesecake. Pop it in the freezer for about 10–15 minutes—this helps it set and keeps everything layered nicely once baking starts.

Step 3: Whip up the creamy cheesecake filling

In a large mixing bowl, beat the softened cream cheese with granulated sugar until smooth and fluffy—no lumps! Then add in the eggs one at a time, mixing slowly to keep the batter smooth. Next, fold in the sour cream and vanilla extract until everything is perfectly combined. This part is crucial for that rich, velvety texture you want from your cheesecake.

Step 4: Bake your cheesecake in a water bath

Pour the cheesecake filling gently over the crust and pineapple. Use a spatula to smooth the top evenly. Now, place your springform pan in a larger pan filled halfway with hot water—a water bath prevents cracks and keeps everything moist while baking. Bake for 60 to 70 minutes, until the center is mostly set but still slightly jiggly. Trust me, this gentle cooking makes all the difference.

Step 5: Cool and chill for the best results

Turn off your oven and open the door slightly, letting the cheesecake cool inside slowly for about an hour. This gradual cooling minimizes cracks too. Once cooled, refrigerate the cheesecake for at least four hours—overnight is even better. The chilling time lets the flavors meld and the layers set perfectly, so don’t skip it!

Step 6: Flip and reveal your masterpiece

When fully chilled, run a thin knife around the edges to loosen the cheesecake from the pan. Then carefully undo the springform and place your serving plate on top. Slowly invert the pan, and watch your beautiful pineapple upside-down cheesecake reveal itself, glistening and ready to impress.

How to Serve Pineapple Upside-Down Cheesecake Recipe

A round cheesecake with three visible layers sits on a white detailed cake stand against a white marbled surface. The bottom layer is a thick, crumbly brown crust. The middle layer is a thick, creamy off-white cheesecake with a smooth texture. The top layer is a shiny, dark caramel glaze that drips slightly down the sides. On the very top, there are circular slices of golden brown pineapple evenly spread, each topped with a bright red maraschino cherry with a stem. In the center, there is a small bunch of fresh green mint leaves. Photo taken with an iphone --ar 4:5 --v 7

Garnishes

For me, a light dusting of powdered sugar over the top adds a subtle sweetness and a pretty finish. Sometimes I add a few fresh mint leaves for color and freshness, which pairs wonderfully with the tropical flavors. If you want extra indulgence, a dollop of whipped cream or a drizzle of caramel sauce works like a charm.

Side Dishes

This Pineapple Upside-Down Cheesecake Recipe shines as a solo dessert but also goes nicely with fresh fruit salad or a scoop of coconut ice cream to keep the tropical vibe going. I’ve also enjoyed it simply with a strong cup of coffee or black tea—perfect for a relaxing afternoon treat.

Creative Ways to Present

For a special occasion, I’ve served this cheesecake on a wooden board surrounded by edible flowers and pineapple wedges for an extra wow factor. Another time, I laid out individual slices with pineapple and cherry skewers for a fun, party-style platter. You can also add toasted coconut flakes on top just before serving to bring a festive texture and look.

Make Ahead and Storage

Storing Leftovers

I always store leftovers in an airtight container in the fridge, which keeps the cheesecake moist and fresh for about 3 to 4 days. If you’re careful flipping the cheesecake back into the pan or wrapping it tightly with plastic wrap, it won’t dry out or absorb fridge odors.

Freezing

I’ve frozen this cheesecake with success by wrapping it tightly in plastic wrap and foil, then thawing overnight in the fridge. It loses just a tiny bit of texture but still tastes delicious. Freezing is great if you want to make it ahead for a large gathering or save leftovers for later.

Reheating

Cheesecake isn’t really meant to be reheated, but if you want a slightly less chilled slice, I pop it out for about 15 minutes at room temperature before serving. This softens the texture and brings out flavors nicely without any risk of drying out or cracking.

FAQs

Can I use fresh pineapple instead of canned in the Pineapple Upside-Down Cheesecake Recipe?

Yes, you can use fresh pineapple, but canned pineapple tends to caramelize more evenly due to its consistent thickness and higher sugar content. If you opt for fresh, slice it as evenly as possible and consider grilling or lightly caramelizing it in a pan before arranging on the cheesecake.
Why do I need to bake the cheesecake in a water bath?

Baking in a water bath helps regulate the temperature around the cheesecake and keeps it moist, which prevents cracks and ensures a smooth, creamy texture. It’s a simple step that makes a big difference in your finished Pineapple Upside-Down Cheesecake Recipe.
Can I make this cheesecake ahead of time?

Absolutely! In fact, I recommend making it a day ahead to let it chill fully and develop more robust flavors. Just make sure to store it covered in the fridge and flip it just before serving.
How do I avoid cracks on my cheesecake?

Slow and gentle baking in a water bath along with gradual cooling in the oven after baking are key. Also, don’t overbeat the cream cheese mixture, and avoid overcooking — when the center jiggles slightly it’s done.
Can I use a regular cake pan instead of a springform pan?

A springform pan is ideal because it releases the sides, making flipping the cheesecake easy without damaging the pineapple topping. If you use a regular pan, you risk the cheesecake breaking when removing or flipping it.

Final Thoughts

This Pineapple Upside-Down Cheesecake Recipe is one of those creations I come back to again and again, especially when I want something a little nostalgic but with a creamy twist. It’s approachable enough for home bakers but impressive enough to serve at celebrations. Plus, the layers of caramelized pineapple, rich cream cheese filling, and crisp crust make every bite memorable. Give it a try—I’m confident it’ll become a favorite in your dessert rotation too!