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Pineapple Upside Down Cheesecake

This delightful dessert combines creamy cheesecake with the vibrant flavors of pineapple and cherries, making it perfect for gatherings and celebrations.
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Prep Time 30 minutes
Cook Time 1 hour 10 minutes
Total Time 8 hours 30 minutes
Servings: 12 servings
Course: Dessert
Cuisine: American, Tropical
Calories: 400
Ingredients Method Notes

Ingredients
  

Cheesecake Base
  • 16 ounces cream cheese, room temp Make sure cream cheese is at room temperature for best results.
  • 1/2 cup granulated sugar
  • 2 large eggs Add eggs one at a time.
  • 1/2 cup sour cream
  • 2 tablespoons pineapple juice
  • 1 teaspoon vanilla extract
Pineapple Topping
  • 1/2 cup unsalted butter, melted Used for greasing pans.
  • 1 cup packed light brown sugar
  • 14 slices canned or fresh pineapple rings
  • 14 pieces maraschino cherries
Cake Batter
  • 1 1/2 cups all-purpose flour, sifted
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 teaspoon salt
  • 3/4 cup light brown sugar, packed
  • 1/4 cup granulated sugar
  • 1 large egg
  • 1/4 cup sour cream
  • 1/2 cup milk
  • 1/4 cup pineapple juice
  • 1 tablespoon vanilla extract

Method
 

Preparing the Cheesecake
  1. Preheat the oven to 325 degrees F. Grease a 9-inch springform pan and wrap it in heavy-duty foil.
  2. In a mixing bowl, whip the cream cheese with granulated sugar until smooth. Then, mix in each egg one at a time until fully combined. Add the sour cream, pineapple juice, and vanilla extract.
  3. Pour the cheesecake mixture into the prepared pan and place it in a roasting dish filled with water. Reduce the oven temperature to 300 degrees F and bake for 45 minutes.
  4. Turn off the oven and leave the cheesecake inside for an additional 20 minutes.
  5. Allow it to cool before refrigerating for at least 8 hours.
Making the Pineapple Topping
  1. Melt butter in two 9-inch pans, then sprinkle the brown sugar, arranging the pineapple rings and maraschino cherries on top.
Baking the Cake
  1. Preheat the oven to 350 degrees F. Combine the dry ingredients in one bowl and mix the wet ingredients in another until smooth.
  2. Combine both mixtures, then divide the batter between the pans and bake for 25-30 minutes.
  3. After cooling for 10 minutes, invert the cakes and layer them with the cheesecake in between.
  4. Serve immediately or chill until ready.

Notes

Consider garnishing each slice with whipped cream or toasted coconut. Best enjoyed within the first couple of days for optimal flavor. Can be stored in an airtight container for up to five days in the fridge.