Pineapple Upside-Down Cheesecake

Name: Pineapple Upside-Down Cheesecake
Prep time: 30 min
Cook time: 1 h 10 min
Total time: 5 h 40 min
Cuisine: American
Ingredients: 1 1/2 cups graham cracker crumbs; 1/4 cup granulated sugar; 6 tablespoons melted butter; 1/2 cup packed brown sugar; 1/4 cup unsalted butter; 10–12 pineapple rings (canned or fresh); Maraschino cherries (one for each ring); 3 (8 oz) blocks cream cheese, softened; 1 cup granulated sugar; 1/2 cup sour cream; 1 teaspoon vanilla extract; 3 large eggs; 1/2 cup crushed pineapple (drained well)

Isabella

🌟Life, Love, and Gastronomy 🍷

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This Pineapple Upside-Down Cheesecake is the perfect tropical twist on the classic cheesecake. With a layer of caramelized pineapple and maraschino cherries on top, it’s as beautiful as it is delicious. The creamy cheesecake filling, paired with a crunchy graham cracker crust, brings everything together for a truly indulgent dessert.

Why You’ll Love This Recipe

I absolutely love how this cheesecake combines two iconic desserts – pineapple upside-down cake and cheesecake – into one irresistible treat. The caramelized pineapple topping adds a rich, buttery sweetness that contrasts beautifully with the smooth, creamy cheesecake filling. The graham cracker crust gives it a satisfying crunch, and the maraschino cherries on top make it feel like a celebration. It’s a showstopper dessert that’s perfect for any occasion, from family gatherings to special events. Plus, it’s surprisingly easy to make despite its impressive appearance.

Ingredients

For the crust:

1 1/2 cups graham cracker crumbs

1/4 cup granulated sugar

6 tablespoons melted butter

For the pineapple topping:

1/2 cup packed brown sugar

1/4 cup unsalted butter

10–12 pineapple rings (canned or fresh)

Maraschino cherries (one for each ring)

For the cheesecake filling:

3 (8 oz) blocks cream cheese, softened

1 cup granulated sugar

1/2 cup sour cream

1 teaspoon vanilla extract

3 large eggs

1/2 cup crushed pineapple (drained well)

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

Directions

Prepare the pineapple topping: In a small saucepan, melt butter and brown sugar over medium heat until it starts to bubble. Pour the mixture into the bottom of a greased 9-inch springform pan. Arrange pineapple rings over the caramel and place a cherry in the center of each ring. Set aside.

Make the crust: In a bowl, mix graham cracker crumbs, sugar, and melted butter until combined. Press the mixture on top of the pineapple rings and slightly up the sides of the pan. Chill in the fridge while you prepare the filling.

Preheat oven: Preheat your oven to 325°F (160°C). Wrap the outside of the springform pan with aluminum foil to prevent leaks. Place it in a larger baking dish for a water bath.

Make the cheesecake filling: In a large bowl, beat the cream cheese and sugar until smooth. Add sour cream and vanilla, mixing well. Add eggs one at a time, beating just until combined. Fold in the drained crushed pineapple.

Assemble and bake: Pour the cheesecake filling over the crust. Place the springform pan into the larger pan and fill with hot water halfway up the sides. Bake for 60–70 minutes or until the center is just set.

Cool and chill: Remove the cheesecake from the water bath and let it cool completely at room temperature. Refrigerate for at least 4 hours or overnight for best results.

Flip and serve: Run a knife around the edges to loosen the cheesecake. Carefully invert onto a serving platter so the pineapples and cherries are on top. Slice and enjoy!

Servings and timing

Prep Time: 30 minutes

Cooking Time: 1 hour 10 minutes

Total Time: 5 hours 40 minutes (includes chilling)

Servings: 12 servings

Calories: 400 kcal per slice

Variations

If you want to mix things up, here are a few variations I love to try with this cheesecake:

Add nuts: Sprinkle crushed pecans or walnuts on top of the crust before baking for added texture and flavor.

Coconut: Add shredded coconut to the pineapple topping for a more tropical flair.

Other fruits: You could switch out the pineapple for other fruits like peaches or berries, but the pineapple really adds a special touch.

Storage/Reheating

To store, I recommend keeping any leftover cheesecake in an airtight container in the fridge for up to 4-5 days. If you need to reheat a slice, just microwave it for 15-20 seconds until warm. This cheesecake also freezes well! Wrap individual slices tightly in plastic wrap and foil and freeze for up to 2 months. To thaw, place it in the fridge overnight.

Related Recipes:

Cranberry Pineapple Upside-Down Cake

FAQs

How do I know when the cheesecake is done baking?

The cheesecake should be slightly jiggly in the center when done. It will continue to set as it cools, so don’t worry if it’s a little soft in the middle. If the edges are set and golden, you’re good to go.

Can I use a different type of crust?

Absolutely! While graham cracker crumbs are classic, I’ve tried using crushed vanilla wafers or even a chocolate cookie crust, and both were delicious alternatives.

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works just as well! Just make sure it’s cut into rings and that you drain any excess juice before using it.

How long should I chill the cheesecake?

I recommend chilling it for at least 4 hours, but overnight is best to allow the flavors to fully develop.

Can I make this cheesecake ahead of time?

Yes, this cheesecake can be made a day or two in advance, making it perfect for parties or gatherings. Just make sure to store it in the fridge until you’re ready to serve.

Conclusion

This Pineapple Upside-Down Cheesecake is the perfect combination of tropical sweetness and rich, creamy cheesecake. The caramelized pineapple topping and crunchy graham cracker crust add incredible texture and flavor, while the smooth filling will have everyone coming back for more. Whether you’re serving it for a special occasion or just because, it’s sure to impress.

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