Pineapple Right Side Up Cheesecake

 

🍍 Pineapple Right Side Up Cheesecake

A Tropical Twist on a Classic Favorite

If you’ve ever fallen in love with the sweet, caramelized flavor of a pineapple upside-down cake, imagine that same tropical goodness meeting the creamy decadence of a classic cheesecake. The result? Pineapple Right Side Up Cheesecake — a dessert that’s every bit as stunning as it is delicious.

This dessert flips the traditional “upside-down” idea on its head, keeping all the signature pineapple-and-cherry charm right on top. With a buttery graham cracker crust, luscious cream cheese filling, and golden caramelized fruit glistening in the spotlight, it’s a showstopper from the very first slice.

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🌞 Why You’ll Love This Cheesecake

This recipe is pure sunshine in dessert form. The tangy-sweet pineapple perfectly complements the creamy richness of the cheesecake, while the brown sugar glaze gives it a nostalgic, caramelized warmth. It’s elegant enough for holidays and celebrations, yet simple enough for a weekend treat.

Whether you’re hosting a dinner party or just craving a tropical escape, Pineapple Right Side Up Cheesecake will bring vacation vibes straight to your kitchen.

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🍍 Ingredients

For the Crust:

• 1 ½ cups graham cracker crumbs

• ¼ cup sugar

• 6 tablespoons unsalted butter, melted

For the Topping:

• ½ cup brown sugar

• 3 tablespoons butter

• 1 (15 oz) can pineapple rings, drained and patted dry

• Maraschino cherries, drained

For the Cheesecake Filling:

• 3 (8 oz) packages cream cheese, softened

• 1 cup granulated sugar

• 3 large eggs

• 1 cup sour cream

• 1 teaspoon vanilla extract

• ½ cup crushed pineapple, well-drained

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👩‍🍳 Directions

1. Prepare the Crust

Preheat your oven to 325°F (160°C).
In a mixing bowl, combine graham cracker crumbs, sugar, and melted butter until evenly coated. Press the mixture firmly into the bottom of a greased 9-inch springform pan. Bake for 10 minutes, then set aside to cool.

2. Caramelize the Pineapple

In a skillet, melt butter and brown sugar over medium heat until bubbly and slightly thickened. Add pineapple rings and cook for about 2–3 minutes on each side until lightly caramelized. Arrange the pineapple rings over the cooled crust and place a cherry in the center of each ring.

3. Make the Cheesecake Filling

In a large bowl, beat cream cheese and sugar together until smooth and creamy. Add eggs one at a time, mixing on low speed after each addition. Stir in sour cream, vanilla extract, and crushed pineapple until fully blended.

4. Assemble and Bake

Pour the cheesecake filling evenly over the pineapple layer. Smooth the top with a spatula.
Bake for 55–65 minutes, or until the center is set but still slightly jiggly. Turn off the oven and let the cheesecake rest inside with the door slightly open for 1 hour.

5. Chill and Serve

Cool completely, then refrigerate for at least 4 hours (overnight is best). To serve, carefully release the springform pan and transfer to a serving plate. Garnish with whipped cream, toasted coconut, or a drizzle of caramel, if desired.

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🍰 Tips for the Perfect Pineapple Cheesecake

• Dry your pineapple rings well before caramelizing to avoid excess moisture.

• Use room temperature cream cheese for a smoother filling.

• Avoid cracks: Don’t overmix the batter, and cool slowly in the oven before chilling.

• Make it fancy: Sprinkle toasted coconut flakes over the top for an extra tropical touch.

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☀️ A Slice of the Tropics

Each bite of Pineapple Right Side Up Cheesecake is pure paradise — buttery crust, creamy filling, and that beautiful caramelized pineapple sweetness that makes it unforgettable. It’s a dessert that looks as good as it tastes and brings a burst of sunshine to any table.

Perfect for summer gatherings, birthdays, or simply to brighten your day, this cheesecake is proof that sometimes the best creations happen when you turn tradition… right side up.