Pineapple Upside Down Cheesecake Recipe

Save this recipe on:

Rich, luscious, and a tropical showstopper—this Pineapple Upside Down Cheesecake is the perfect fusion of two classic desserts. Imagine a buttery, golden crust supporting a velvety cheesecake filling, all crowned with a caramelized layer of pineapple rings and vibrant maraschino cherries. It’s the kind of dessert that turns heads at any gathering, both for its stunning look and unforgettable flavor.

The creamy tang of the cheesecake balances beautifully with the bright, juicy sweetness of pineapple and the nostalgic touch of syrupy cherries. Whether you’re planning a festive celebration or just want to treat yourself to something extraordinary, this recipe promises to impress. It’s a flavor-packed indulgence wrapped in tropical sunshine and old-fashioned comfort.

---

Ingredients for this Pineapple Upside Down Cheesecake

For the pineapple topping:

• 1/4 cup unsalted butter, melted
• 1/2 cup packed light brown sugar
• 7–9 pineapple slices (canned or fresh)
• 7–9 maraschino cherries

For the graham cracker crust:

• 1 and 1/2 cups graham cracker crumbs
• 1/4 cup granulated sugar
• 1/2 cup unsalted butter, melted

For the cheesecake filling:

• 3 packages (8 oz each) cream cheese, softened
• 3/4 cup granulated sugar
• 3 large eggs
• 1 teaspoon vanilla extract
• 1/2 cup sour cream
• 1 tablespoon all-purpose flour

---

Step 1: Prepare the Pineapple Layer

Preheat your oven to 325°F (163°C). Lightly grease a 9-inch springform pan and line the bottom with parchment paper. Pour the melted butter into the pan and swirl to coat the bottom evenly. Sprinkle brown sugar over the butter layer. Arrange the pineapple slices over the sugar, placing one in the center and the rest in a circular pattern. Place a maraschino cherry in the center of each pineapple ring. Set the pan aside.

---

Step 2: Make the Graham Cracker Crust

In a mixing bowl, combine graham cracker crumbs and sugar. Add melted butter and mix until the texture resembles wet sand. Press the mixture firmly into the pan on top of the pineapples, creating an even crust layer. Use the bottom of a measuring cup or glass to press it down tightly. Place the crust in the freezer while you prepare the filling.

---

Step 3: Prepare the Cheesecake Filling

In a large bowl, beat the cream cheese until smooth and fluffy. Add the sugar and beat until well combined. Mix in eggs one at a time, scraping down the sides of the bowl after each addition. Add vanilla extract, sour cream, and flour, and mix until just incorporated. Avoid overbeating to prevent air bubbles.

---

Step 4: Assemble and Bake

Take the crust from the freezer and gently pour the cheesecake batter over it. Smooth the top with a spatula. Wrap the bottom of the springform pan in aluminum foil to prevent leaks and place it into a larger baking dish. Add hot water around the springform pan to create a water bath. Bake for 55–65 minutes, or until the center is set but still slightly jiggly.

---

Step 5: Cool and Chill

Turn off the oven and leave the cheesecake inside with the door slightly open for 1 hour. Remove from the water bath and let it cool completely on a wire rack. Then refrigerate for at least 4 hours or overnight. When ready to serve, run a knife around the edge of the cheesecake before unlocking the springform pan. Invert the cheesecake onto a serving plate to reveal the gorgeous pineapple topping.

---

Estimated Nutrition

Per slice (based on 12 servings)

• Calories: 420
• Total Fat: 28g
• Saturated Fat: 16g
• Cholesterol: 115mg
• Sodium: 280mg
• Total Carbohydrates: 36g
• Sugar: 29g
• Protein: 6g

(Note: Nutritional values may vary depending on ingredient brands and portion size.)

---

Frequently Asked Questions

1. Can I use fresh pineapple instead of canned?

Absolutely! Just make sure the slices are similar in size and thickness to canned rings so they cook evenly.

2. Do I need a water bath for this recipe?

Yes, it helps prevent cracking and ensures the cheesecake cooks evenly with a creamy texture.

3. What if I don’t have a springform pan?

A deep cake pan can work, but removing the cheesecake cleanly will be trickier. Line it with parchment paper for easier release.

4. How do I know when the cheesecake is done baking?

The edges should be set while the center still jiggles slightly when shaken. It will firm up as it cools.

5. Can I make this cheesecake in advance?

Yes! It’s actually better after chilling overnight, making it perfect for prepping a day ahead.

6. Why did my cheesecake crack?

Overmixing the batter or skipping the water bath can cause cracks. Also, cooling too quickly can lead to surface cracks.

7. Can I make this gluten-free?

You can substitute gluten-free graham crackers for the crust. Ensure all other ingredients are gluten-free certified.

8. What can I use instead of sour cream?

Greek yogurt is a great substitute with a similar tangy flavor and creamy consistency.

---

Print

Save this recipe on: