Name: Pineapple Upside-Down Cheesecake Recipe
Prep time: 25 min
Cook time: 1 h 10 min
Total time: 1 h 35 min
Cuisine: American
Ingredients: 1 1/2 cups graham cracker crumbs; 1/4 cup unsalted butter, melted; 1/2 cup brown sugar; 6 to 8 pineapple rings, canned or fresh; 6 to 8 maraschino cherries; Melted butter for drizzling (approx. 2 tablespoons); 24 ounces cream cheese, softened; 3/4 cup granulated sugar; 1/2 cup sour cream; 1 teaspoon vanilla extract; 3 large eggs

If you’re craving something that feels both tropical and indulgent, you absolutely have to try this Pineapple Upside-Down Cheesecake Recipe. It’s the perfect marriage of two classic desserts—the luscious creaminess of cheesecake paired with the caramelized, buttery pineapple and cherry topping you know and love from a traditional upside-down cake. Every bite brings a balance of tangy sweetness and rich texture that’s just spectacular.

I remember making this for the first time at a summer gathering, and honestly, it stole the show. It’s special because it’s a showstopper that’s surprisingly easy to pull off. Whether you’re celebrating a birthday, hosting a barbecue, or just want a unique dessert to impress your friends, this Pineapple Upside-Down Cheesecake Recipe will become your go-to. Plus, you’ll love how the flavors meld together overnight, making morning prep super easy if you plan ahead.

Ingredients You’ll Need

Each ingredient here plays a key role in bringing out the best in this Pineapple Upside-Down Cheesecake Recipe, combining classic cheesecake richness with that caramelized tropical flair. I find that using the right type of pineapple and a lovely buttery crust really make all the difference.

Graham cracker crumbs: This gives the crust a sweet, slightly crunchy base that perfectly complements the creamy filling.
Unsalted butter: Melting this blends beautifully with the graham crackers and also helps caramelize the pineapple topping.
Brown sugar: Essential for that deep caramel flavor on the pineapple layer—don’t skip it!
Pineapple rings: I recommend canned for perfect caramelization and consistent slices, but fresh works if you prefer.
Maraschino cherries: These add a fun pop of color and sweetness right in the center of each pineapple ring.
Cream cheese: Softened and smooth, it’s the heart of the cheesecake layer—make sure it’s room temperature for ease.
Granulated sugar: Sweetens the creamy cheesecake without overpowering it.
Sour cream: Adds that subtle tang and silky texture that makes cheesecake so dreamy.
Vanilla extract: A simple but important flavor enhancer that rounds out the cheesecake’s taste.
Large eggs: They bind everything and give cheesecake its rich, custardy feel.

Variations

I like to switch things up with this Pineapple Upside-Down Cheesecake Recipe depending on the occasion. It’s super flexible, so don’t hesitate to tailor it to your tastes or dietary needs—it’s your dessert, after all!

Gluten-free variation: Swap in gluten-free graham crackers or crushed gluten-free cookies for the crust. I’ve done this several times for friends, and the texture stays delightful.
Tropical twist: Add shredded coconut either into the crust or on top after baking for an extra island vibe.
Mini cheesecakes: Make individual-sized portions using a muffin tin lined with cupcake liners—perfect for parties and easier to serve.
Low-sugar option: Try using a sugar substitute like erythritol, especially in the crust and cheesecake filling, to reduce sweetness without losing flavor.

How to Make Pineapple Upside-Down Cheesecake Recipe

Step 1: Prepare the Pineapple Layer and Caramel Base

First things first, preheat your oven to 325°F and grease a springform pan thoroughly. Sprinkle that brown sugar evenly across the bottom—this will melt into a beautiful caramel as it bakes. Now, carefully arrange your pineapple rings on top of the sugar and place a maraschino cherry right in the center of each ring. Drizzle some melted butter over the entire layer—that buttery richness is crucial to caramelizing the fruit perfectly. Don’t rush this step; even layering means an even caramel layer.

Step 2: Make and Chill the Crust

Combine the graham cracker crumbs with melted butter until you have crumbly, wet sand texture. Press this mixture gently but firmly over the pineapple and brown sugar layer. I find that pressing with the bottom of a glass works great for even pressure. Then, pop the pan in the freezer for 10 to 15 minutes—that chilling helps keep the crust firm and stops it from slipping when you pour in the cheesecake batter.

Step 3: Mix the Cheesecake Filling

Grab a large mixing bowl and beat the softened cream cheese with granulated sugar until smooth—no lumps here, it should be silky. Add the eggs one at a time, mixing slowly to avoid incorporating too much air that could cause cracks. Then stir in sour cream and vanilla extract until the whole mixture is creamy and just combined. Resist overmixing to keep your cheesecake dense and luxurious.

Step 4: Bake in a Water Bath for Perfect Texture

Pour the cheesecake batter gently over the crust and pineapple, smoothing the top with a spatula. Now, the water bath: this little trick saved me many cracked cheesecakes. Place the springform pan in a larger roasting pan and add boiling water halfway up the sides of your cake pan. Bake for 60 to 70 minutes, until the center is almost set but still jiggles slightly when nudged. This slow, moist bake keeps the cheesecake creamy without cracks.

Step 5: Cool and Chill Overnight

After baking, turn off the oven and crack the door open to let the cheesecake cool gradually for about an hour—this helps prevent sudden temperature changes that can cause cracks. Then refrigerate it for at least 4 hours, or I prefer overnight. This resting time is crucial because it lets the flavors meld and the layers solidify, making it so much easier to flip and serve without damage.

Step 6: Flip and Serve

Once completely chilled, run a knife carefully around the edges to loosen the cheesecake from the pan. Release the springform sides, place a serving plate over the pan bottom, and quickly invert. This is the ‘wow’ moment where the caramelized pineapple and cherries become the star of the show. Be gentle and trust the chill time—you’ll get a clean flip every time!

How to Serve Pineapple Upside-Down Cheesecake Recipe

A round pineapple upside-down cheesecake is shown on a white cake stand with intricate patterns. It has three visible layers: a crumbly brown base, a thick creamy light yellow cheesecake layer in the middle, and a shiny caramelized top layer. The top layer is decorated with glossy caramelized pineapple rings and bright red cherries with stems placed on each ring around the edge. In the center, there is a small bunch of fresh green mint leaves. Some caramel sauce is dripping down the cheesecake’s sides. The background is a white marbled texture with blurred white plates stacked in the back. Photo taken with an iphone --ar 4:5 --v 7

Garnishes

I love adding a dollop of freshly whipped cream on each slice—it cuts through the sweetness nicely and adds a soft contrast. Sometimes, I sprinkle toasted coconut flakes on top for extra texture and that tropical feel. A mint leaf is a simple, fresh garnish that makes each slice look Pinterest-perfect, and trust me, your guests will notice.

Side Dishes

This cheesecake pairs beautifully with a cup of strong coffee or a chilled glass of dessert wine. If you’re doing a full meal, light fruit salads or a tropical salsa with mango and lime are refreshing companions that balance the richness of the cheesecake.

Creative Ways to Present

For summer parties, try serving this Pineapple Upside-Down Cheesecake Recipe in individual jars or clear cups, layering pineapple, cheesecake, and crust for a deconstructed effect. Another fun idea is to top the slices with grilled pineapple rings for an extra charred flavor that really elevates the dessert for special occasions.

Make Ahead and Storage

Storing Leftovers

I keep leftovers covered tightly with plastic wrap or in an airtight container and refrigerate for up to 4 days. The flavors actually deepen after sitting, so sometimes I’m glad it lasts that long. Just make sure it stays cold and the topping remains moist and glossy.

Freezing

Freezing works well if you cut the cheesecake into slices first. Wrap each slice in plastic wrap and foil, then freeze for up to 2 months. When you’re ready to enjoy, thaw overnight in the fridge to maintain that creamy texture without condensation ruining the caramel topping.

Reheating

Honestly, I prefer this cheesecake cold or at room temperature rather than reheated. If you want it a bit warmer, take it out of the fridge about 30 minutes before serving so it softens up naturally. Reheating in a microwave tends to mess with the texture here.

FAQs

Can I use fresh pineapple instead of canned for this Pineapple Upside-Down Cheesecake Recipe?

Yes, you can use fresh pineapple rings. Just be sure to slice them evenly and pat dry to reduce excess moisture that could affect caramelization. Canned pineapple tends to have a more consistent texture and caramelizes more predictably, which is why I usually recommend it.
Why do I need to bake this cheesecake in a water bath?

Baking in a water bath adds moisture to the oven environment and helps the cheesecake cook evenly. This prevents cracks on the surface—a common problem with cheesecakes—and results in that smooth, creamy texture we all want.
Can I make this Pineapple Upside-Down Cheesecake Recipe ahead of time?

Absolutely! In fact, I recommend making it the day before serving. Letting it chill overnight not only helps the cheesecake set perfectly but also allows the flavors to deepen, making every bite even better.
How do I prevent the crust from getting soggy?

Pressing the graham cracker crust firmly and chilling it before adding the filling helps create a barrier so the crust stays crisp longer. Also, using melted butter mixed evenly in the crumbs seals them somewhat against moisture from the filling.
What’s the best way to serve this Pineapple Upside-Down Cheesecake Recipe?

I love serving it chilled with a little whipped cream on top and a sprinkle of toasted coconut or a fresh mint leaf. Pairing it with a fruity side or coffee rounds out the experience perfectly.

Final Thoughts

This Pineapple Upside-Down Cheesecake Recipe has quickly become one of my favorite desserts to make and share. There’s something magic about that golden caramelized pineapple topping combined with the creamy, smooth cheesecake that’s just pure comfort on a plate. I hope you find it as rewarding to make as I do, and that it brings a little tropical sunshine to your table whenever you decide to whip it up. Give it a try—you’ll love the layers of flavor and the smiles it brings!