Pineapple upside-down cheesecake is a tropical twist on two classic desserts, combining the caramelized pineapple topping of an upside-down cake with the rich creaminess of a cheesecake. The result?

A stunning, golden dessert that’s as refreshing as a beachside getaway. With its buttery caramel glaze, sweet pineapple slices, and velvety cheesecake base, this dessert is perfect for summer parties or when you want a taste of sunshine no matter the season.

I first whipped up this cheesecake for a backyard barbecue, and it was the star of the dessert table.

The tangy pineapple pairs beautifully with the creamy cheesecake, creating a flavor balance that feels indulgent yet light.

The caramelized topping adds just the right amount of sweetness and visual flair, making it a guaranteed showstopper.

Pair this dreamy dessert with a refreshing piñagf colada or a vibrant mango kiwi smoothie to double down on the tropical vibes. These drinks complement the cheesecake’s flavors perfectly and add a fun, fruity twist to your table.

Give this pineapple upside-down cheesecake a try and let me know how it brings a tropical touch to your celebrations. I’d love to hear about your serving ideas or creative variations!

What’s so Special About This Dish?

Knife running around the edges of the cheesecake inside the pan on a white marble cooktop. The cheesecake cools before being inverted onto a serving plate and placed in the refrigerator for 3 hours to set before serving.

Tropical Flavors: The caramelized pineapple topping adds a sweet, tangy burst of sunshine to every bite.
Decadent & Creamy: The velvety cheesecake base melts in your mouth, balancing the fruity topping beautifully.
Visually Stunning: The golden pineapple slices and caramel glaze make this dessert as gorgeous as it is delicious.
Perfect for Gatherings: Whether it’s a barbecue or a dinner party, this cheesecake steals the show.

Cheesecake pan in the oven, baking at 325°F (165°C), with the cheesecake filling nearly set in the center after 55–60 minutes. The edges are lightly browned, and the top of the cheesecake is slightly puffed up, ready to cool.

Pineapple Upside-Down Cheesecake Recipe

This Pineapple Upside-Down Cheesecake blends the classic flavors of caramelized pineapple and cherries with a rich, creamy cheesecake. A delightful dessert that’s perfect for any occasion!

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Prep Time 25

Cook Time 55

Additional Time 3 30

Total Time 4 50

Course Dessert

Cuisine American

Servings 8

Calories 599 kcal

Equipment

9-inch round cake pan
Mixing bowls (small and medium)
Electric Mixer or Hand Mixer
Knife
Serving plate

Ingredients

5 tablespoons butter melted, divided
2 tablespoons brown sugar
7 to 8 canned pineapple slices drained
7 maraschino cherries drained and stemmed
1 cup graham cracker crumbs
3 tablespoons white sugar
3 8 ounce packages cream cheese, softened
¾ cup white sugar
¾ cup sour cream
2 teaspoons vanilla extract
3 eggs

Instructions

Preheat oven to 325°F (165°C). Mix 2 tablespoons butter and brown sugar in a 9-inch round cake pan. Spread evenly, then arrange pineapple slices and cherries on top.
Combine graham cracker crumbs, 3 tablespoons sugar, and 3 tablespoons melted butter. Press mixture over pineapples.
Beat cream cheese and 3/4 cup sugar until smooth. Mix in sour cream and vanilla, then add eggs one at a time, blending on low speed.
Pour the cream cheese mixture into the prepared pan and bake for 55–60 minutes, until almost set in the center.
Run a knife around the edges to loosen and cool completely (30 minutes). Invert onto a serving plate and refrigerate for at least 3 hours before serving.