Tropical Pineapple Upside-Down Cheesecake

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Bring a taste of the tropics to your dessert table with this stunning Pineapple Upside-Down Cheesecake. This recipe blends the silky richness of classic cheesecake with the glossy, caramelized fruit topping of an upside-down cake. Each slice is creamy, vibrant, and beautifully layered—making it perfect for holidays, gatherings, or anytime you want a showstopping dessert that feels like a celebration.

The buttery graham cracker crust, sweet caramelized pineapple rings, and velvety cheesecake filling come together for a mouthwatering treat that looks impressive but is surprisingly simple to prepare.

Ingredients

For the Pineapple Topping

• ½ cup brown sugar
• 6–8 pineapple rings (canned or fresh)
• 6–8 maraschino cherries
• ¼ cup unsalted butter, melted

For the Crust

• 1 ½ cups graham cracker crumbs
• ¼ cup unsalted butter, melted

For the Cheesecake Filling

• 24 oz cream cheese, softened
• ¾ cup granulated sugar
• 3 large eggs
• ½ cup sour cream
• 1 teaspoon vanilla extract

Instructions

1. Prepare the Pineapple Layer

1. Preheat the oven to 325°F (163°C).
2. Grease a springform pan.
3. Sprinkle brown sugar evenly over the bottom.
4. Arrange pineapple rings in a single layer and place a cherry in each center.
5. Drizzle melted butter over the fruit.

2. Make the Crust

1. Mix graham cracker crumbs with melted butter.
2. Press the mixture gently over the pineapple layer.
3. Freeze for 10–15 minutes to help it firm up.

3. Prepare the Cheesecake Filling

1. Beat cream cheese and sugar until smooth.
2. Add eggs one at a time, mixing slowly.
3. Add sour cream and vanilla; mix until creamy and combined.

4. Assemble the Cheesecake

1. Pour the cheesecake filling over the chilled crust and pineapple layer.
2. Smooth the top with a spatula.

5. Bake

1. Place the springform pan in a water bath.
2. Bake for 60–70 minutes, until the center is almost set but slightly jiggly.

6. Cool and Chill

1. Turn off the oven, crack the door, and let it cool for 1 hour.
2. Refrigerate for at least 4 hours or overnight.

7. Invert and Serve

1. Run a knife around the edge.
2. Release the springform pan.
3. Carefully invert the cake onto a serving plate to reveal the caramelized pineapple topping.

Pro Tips

• Use canned pineapple for consistent shape and natural sweetness.
• A water bath helps achieve a perfectly smooth, crack-free cheesecake.
• Chill completely before flipping—overnight is best.
• Run a warm knife through each slice for clean cuts.

Why This Recipe Works

• Combines two iconic desserts into one irresistible treat.
• Gorgeous caramelized fruit topping that makes a stunning presentation.
• Creamy filling paired with buttery crust creates perfect texture contrast.
• Great for entertaining—feeds a crowd and can be made ahead.

Substitutions & Variations

• Fresh pineapple: Slice thinly and sauté briefly in butter and sugar before using.
• Crust swap: Try vanilla wafer crumbs, digestive biscuits, or shortbread.
• Flavor twist: Add coconut extract or shredded coconut for island-inspired flavor.
• Cherry alternative: Use fresh raspberries or no fruit at all for a simpler look.

Make-Ahead, Storage & Reheating Guide

Make-Ahead

• Prepare the cheesecake 1–2 days ahead for best texture and easier slicing.

Storage

• Store in the refrigerator, tightly covered, for up to 5 days.
• Freeze individual slices for up to 2 months. Thaw overnight in the fridge.

Reheating

• This dessert is served chilled—no reheating needed.
• To refresh frozen slices, thaw and serve cold.

Serving Ideas

• Fresh whipped cream or coconut whipped cream
• Toasted macadamia nuts or pecans for crunch
• Caramel or vanilla sauce drizzle
• Grilled pineapple slices
• Coffee, iced latte, or tropical fruit punch

Nutrition (Per Serving Estimate)

• Calories: 410
• Fat: 28g
• Saturated Fat: 16g
• Carbohydrates: 35g
• Sugar: 29g
• Protein: 6g
• Fiber: 1g
• Sodium: 230mg
• Cholesterol: 115mg

Frequently Asked Questions

1. Can I use fresh pineapple instead of canned?

Yes! Slice it thinly and consider lightly cooking it in butter and sugar to help soften and caramelize.

2. Is a water bath necessary?

Strongly recommended. It ensures even baking and helps keep the cheesecake smooth.

3. How do I keep the crust from getting soggy?

Chilling the crust before adding the filling helps keep it firm and stable.

4. Can this cheesecake be made ahead?

Absolutely—this is a perfect make-ahead dessert since it requires chilling time.

5. How long should it chill before flipping?

At least 4 hours, but overnight chilling gives the best results.

This Pineapple Upside-Down Cheesecake is a tropical twist on classic comfort. With a caramelized fruit topping, creamy filling, and buttery crust, it’s a beautiful and delicious dessert that always impresses. Whether you’re hosting a celebration or treating yourself to something special, this recipe brings sunshine and flavor to every bite.

Pineapple Upside-Down Cheesecake

Creamy cheesecake meets caramelized pineapple in this stunning upside-down dessert. Perfect for parties, holidays, and tropical-inspired celebrations.

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Prep Time 25 minutes mins

Cook Time 1 hour hr 10 minutes mins

Total Time 1 hour hr 35 minutes mins

Course Dessert

Cuisine American

Servings 12

Calories 410 kcal

Ingredients

  

For the Pineapple Topping

• ½ cup brown sugar
• 6-8 pineapple rings (canned or fresh)
• 6-8 maraschino cherries
• ¼ cup unsalted butter, melted

For the Crust

• 1 ½ cups graham cracker crumbs
• ¼ cup unsalted butter, melted

For the Cheesecake Filling

• 24 oz cream cheese, softened
• ¾ cup granulated sugar
• 3 large eggs
• ½ cup sour cream
• 1 tsp vanilla extract

Instructions

 

1. Prepare the Pineapple Layer

• Preheat the oven to 325°F (163°C).
• Grease a springform pan.
• Sprinkle brown sugar evenly over the bottom.
• Arrange pineapple rings in a single layer and place a cherry in each center.
• Drizzle melted butter over the fruit.

2. Make the Crust

• Mix graham cracker crumbs with melted butter.
• Press the mixture gently over the pineapple layer.
• Freeze for 10–15 minutes to help it firm up.

3. Prepare the Cheesecake Filling

• Beat cream cheese and sugar until smooth.
• Add eggs one at a time, mixing slowly.
• Add sour cream and vanilla; mix until creamy and combined.

4. Assemble the Cheesecake

• Pour the cheesecake filling over the chilled crust and pineapple layer.
• Smooth the top with a spatula.

5. Bake

• Place the springform pan in a water bath.
• Bake for 60–70 minutes, until the center is almost set but slightly jiggly.

6. Cool and Chill

• Turn off the oven, crack the door, and let it cool for 1 hour.
• Refrigerate for at least 4 hours or overnight.

7. Invert and Serve

• Run a knife around the edge.
• Release the springform pan.
• Carefully invert the cake onto a serving plate to reveal the caramelized pineapple topping.

Notes

• For the cleanest slices, chill overnight before serving.
• Canned pineapple produces the most consistent results.
• Always invert carefully to keep the fruit layer intact.

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