Pineapple Upside-Down Cheesecake – A Tropical Delight!

If you love the classic pineapple upside-down cake and rich, creamy cheesecake, this Pineapple Upside-Down Cheesecake is the perfect dessert! With buttery caramelized pineapple slices on top, a smooth cheesecake layer, and a delicious graham cracker crust, this treat is sure to impress at any gathering.

Why You’ll Love This Recipe

✔ A Unique Twist – Combines the best of pineapple upside-down cake and cheesecake.
✔ Tropical & Sweet – The perfect balance of creamy and fruity flavors.
✔ Great for Any Occasion – Perfect for summer parties, holidays, or just a weekend treat.

Ingredients

For the Pineapple Topping:

5 Tbsp melted butter
2 Tbsp brown sugar
2 (8-ounce) cans of pineapple slices
Maraschino cherries (for garnish)

For the Cheesecake Filling:

2 (8-ounce) packages of cream cheese, softened
¾ cup granulated sugar
2 large eggs
1 tsp vanilla extract
½ cup sour cream

For the Crust:

1 ½ cups graham cracker crumbs
5 Tbsp melted butter
¼ cup granulated sugar

Step-by-Step Instructions

Step 1: Prepare the Pineapple Layer

Preheat oven to 325°F (163°C).
Grease a 9-inch springform pan.
Pour melted butter into the bottom of the pan and sprinkle with brown sugar.
Arrange pineapple slices in a single layer on top of the butter mixture.
Place maraschino cherries in the center of each pineapple slice.

Step 2: Make the Cheesecake Crust

In a bowl, mix graham cracker crumbs, melted butter, and sugar until well combined.
Press the mixture firmly into the bottom and slightly up the sides of the pan.

Step 3: Prepare the Cheesecake Filling

Beat cream cheese and sugar together until smooth and creamy.
Add eggs, one at a time, mixing after each addition.
Stir in vanilla extract and sour cream, mixing until just combined.

Step 4: Assemble & Bake

Pour the cheesecake batter over the pineapple slices in the pan.
Place the cheesecake pan inside a larger roasting pan and pour hot water around it (about 1 inch deep) for a water bath.
Bake for 50-60 minutes, or until the center is slightly jiggly but set.

Step 5: Cool & Serve

Let the cheesecake cool in the oven with the door slightly open for 30 minutes.
Transfer to the fridge and chill for at least 4 hours or overnight.
Once chilled, carefully invert onto a serving plate so the pineapple layer is on top.
Slice and enjoy!

Serving Tips

🍍 Serve chilled or at room temperature.
🍒 Garnish with whipped cream or extra cherries for a beautiful presentation.
🍯 Drizzle with caramel sauce for extra indulgence.

Storage & Make-Ahead Tips

Store leftovers in an airtight container in the fridge for up to 4 days.
Freeze individual slices for up to 2 months. Wrap tightly in plastic wrap and foil before freezing.

Final Thoughts

This Pineapple Upside-Down Cheesecake is a show-stopping dessert that blends the buttery caramelized pineapple flavors with rich, velvety cheesecake. Whether you’re serving it at a party or making it for a special treat, it’s guaranteed to be a crowd favorite!