Pineapple Upside-Down Cheesecake – A Tropical Twist on Two Classics!

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This stunning dessert combines the caramelized sweetness of pineapple upside-down cake with the creamy richness of cheesecake—all in one showstopping treat! A buttery brown sugar-pineapple topping sits atop a velvety vanilla cheesecake layer, making it perfect for summer parties, holidays, or anytime you crave a taste of the tropics.

Why You’ll Love This Recipe

✅ Best of Both Worlds – Tropical pineapple meets decadent cheesecake
✅ Make-Ahead Friendly – Tastes even better chilled overnight
✅ Impressive Presentation – Gorgeous caramelized pineapple design
✅ No Water Bath Needed – Simple baking method

Ingredients

For the Pineapple Layer:

  • ¼ cup unsalted butter, melted
  • ½ cup packed brown sugar
  • 1 (20 oz) can pineapple slices, drained (reserve juice)
  • 10-12 maraschino cherries

For the Cheesecake Layer:

  • 3 (8 oz) blocks cream cheese, softened
  • ¾ cup granulated sugar
  • 3 large eggs, room temperature
  • ¼ cup reserved pineapple juice (or milk)
  • 2 tsp vanilla extract
  • 1 tbsp all-purpose flour (optional, for stability)

For the Crust (Optional):

  • 1 ½ cups graham cracker crumbs
  • 3 tbsp melted butter
  • 1 tbsp sugar

Step-by-Step Instructions

Step 1: Prep the Pineapple Topping

  1. Preheat oven to 325°F (160°C).
  2. Mix melted butter and brown sugar, then spread evenly in a 9-inch springform pan.
  3. Arrange pineapple slices over the sugar mixture and place cherries in the centers.

Step 2: Make the Cheesecake Batter

  1. Beat cream cheese and sugar until smooth.
  2. Add eggs one at a time, then mix in pineapple juice, vanilla, and flour (if using).

Step 3: Add Crust (If Using)

  1. Mix graham crumbs, butter, and sugar, then press over the pineapple layer.
  2. Skip this step for a crustless version!

Step 4: Bake & Chill

  1. Pour cheesecake batter over the pineapple layer.
  2. Bake 50-60 minutes until edges are set but center jiggles slightly.
  3. Cool 1 hour at room temp, then refrigerate at least 4 hours (overnight best).

Step 5: Flip & Serve

  1. Run a knife around the edges, then invert onto a serving plate.
  2. Lift pan slowly to reveal the beautiful pineapple design!

Tips for Success

🔹 For Clean Slices – Dip knife in hot water before cutting.
🔹 Extra Flavor – Add 1 tsp cinnamon or ½ cup toasted coconut to the crust.
🔹 No Canned Pineapple? Use fresh pineapple (sauté in butter/sugar first).

Serving Suggestions

  • Top with whipped cream and toasted coconut flakes.
  • Drizzle with caramel sauce for extra decadence.

Final Thoughts

This Pineapple Upside-Down Cheesecake is a tropical vacation on a plate—creamy, caramelized, and utterly unforgettable. Perfect for special occasions or when you want to impress!

Slice into paradise! 🍍🍰✨

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