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Pineapple Upside-Down Cheesecake dessert with caramelized pineapple

Pineapple Upside-Down Cheesecake

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  • Author: Ashley
  • Prep Time: 25 minutes
  • Cook Time: 70 minutes
  • Total Time: 95 minutes + chilling
  • Yield: 10 to 12 servings 1x
  • Category: Dessert
  • Method: Baked
  • Cuisine: American
  • Diet: Vegetarian

Description

This Pineapple Upside-Down Cheesecake brings together the best of two classic desserts — a rich, creamy cheesecake layered over caramelized pineapple rings and sweet cherries. With a buttery graham cracker crust and a silky vanilla filling, it’s a showstopping tropical treat that’s perfect for holidays, parties, or when you just want an easy recipe that feels like a celebration.


Ingredients

Scale
  • 1 1/2 cups graham cracker crumbs
  • 1/4 cup unsalted butter, melted
  • 1/2 cup brown sugar
  • 6 to 8 pineapple rings, canned or fresh
  • 6 to 8 maraschino cherries
  • 24 ounces cream cheese, softened
  • 3/4 cup granulated sugar
  • 1/2 cup sour cream
  • 1 teaspoon vanilla extract
  • 3 large eggs

Instructions

1. Preheat oven to 325°F. Grease a springform pan and sprinkle brown sugar evenly on the bottom. Arrange pineapple rings and place a cherry in the center of each. Drizzle with melted butter.

2. Mix graham cracker crumbs with melted butter. Press over the pineapple layer. Freeze for 10–15 minutes.

3. In a large bowl, beat cream cheese and sugar until smooth. Add eggs one at a time, mixing slowly.

4. Add sour cream and vanilla extract. Mix until fully combined and smooth.

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

6. Place pan in a water bath and bake for 60–70 minutes until center is mostly set.

7. Turn off oven, crack the door, and let cheesecake cool gradually for 1 hour.

8. Refrigerate for at least 4 hours or overnight.

9. Once fully chilled, run a knife around the edge, release springform, and carefully invert onto serving plate.


Notes

Use canned pineapple for best caramelization and even slices.

Always bake cheesecake in a water bath to avoid cracks.

Let it chill overnight before flipping to keep the layers intact.


Nutrition

  • Serving Size: 1 slice
  • Calories: 410
  • Sugar: 29g
  • Sodium: 230mg
  • Fat: 28g
  • Saturated Fat: 16g
  • Unsaturated Fat: 11g
  • Trans Fat: 0g
  • Carbohydrates: 35g
  • Fiber: 1g
  • Protein: 6g
  • Cholesterol: 115mg