Pineapple Right Side Up Cheesecake – A Deliciously Tropical Dessert

If you love the flavors of pineapple upside-down cake and classic cheesecake, why not combine them into one incredible dessert? This Pineapple Right Side Up Cheesecake is a tropical, creamy, and indulgent treat that takes traditional cheesecake to a whole new level. The caramelized pineapple topping, rich cream cheese filling, and buttery graham cracker crust create an irresistible combination that will leave everyone asking for seconds.

In this guide, we’ll cover everything you need to know to make this show-stopping dessert, from choosing the right ingredients to step-by-step baking instructions. Let’s get started!

Why You’ll Love This Recipe

  • Perfect Blend of Flavors – The sweet and tangy pineapple pairs beautifully with the rich and creamy cheesecake.
  • Visually Stunning – The golden pineapple rings and bright cherries make this a gorgeous centerpiece for any occasion.
  • Make-Ahead Friendly – This cheesecake needs to chill for several hours, making it a great dessert to prepare in advance.
  • Crowd-Pleasing Dessert – Whether it’s a holiday, birthday, or casual gathering, this cheesecake is sure to impress!

Ingredients Breakdown

For the Crust:

  • 2 cups graham cracker crumbs – Creates a sturdy, buttery base.
  • ½ cup unsalted butter, melted – Helps bind the crumbs together.
  • ¼ cup granulated sugar – Adds a touch of sweetness.

For the Pineapple Topping:

  • 1 can (20 oz) pineapple slices, drained – The star of the show!
  • ½ cup brown sugar – Creates a caramelized, sticky-sweet layer.
  • ¼ cup unsalted butter, melted – Enhances the caramelization process.
  • 8-10 maraschino cherries – Adds a pop of color and flavor.

For the Cheesecake Filling:

  • 3 (8 oz) packages cream cheese, softened – The foundation of a rich, smooth cheesecake.
  • 1 cup granulated sugar – Balances the tanginess of the cream cheese.
  • 3 large eggs – Provides structure and creaminess.
  • 1 teaspoon vanilla extract – Enhances the overall flavor.
  • ½ cup sour cream – Adds a slight tang and smooth texture.
  • ¼ cup pineapple juice (reserved from the canned pineapple) – Infuses tropical flavor into the filling.
  • 2 tablespoons all-purpose flour – Helps stabilize the cheesecake.

Step-by-Step Instructions

1. Preheat and Prepare

Preheat your oven to 325°F (163°C). Grease a 9-inch springform pan to prevent sticking.

2. Make the Pineapple Topping

  • Pour melted butter into the bottom of the pan.
  • Sprinkle brown sugar evenly over the butter.
  • Arrange the pineapple slices in a single layer on top of the sugar.
  • Place a maraschino cherry in the center of each pineapple ring.

3. Prepare the Crust

  • In a bowl, mix graham cracker crumbs, melted butter, and sugar until combined.
  • Press the mixture firmly over the pineapple layer in the pan.
  • Set aside while preparing the filling.

4. Make the Cheesecake Filling

  • In a large mixing bowl, beat cream cheese and sugar until smooth.
  • Add eggs one at a time, mixing after each addition.
  • Stir in vanilla extract, sour cream, pineapple juice, and flour until fully combined.
  • Pour the cheesecake batter over the crust and pineapple layer.
  • Tap the pan gently on the counter to remove air bubbles.

5. Bake the Cheesecake

  • Bake for 50-55 minutes, or until the center is set but slightly jiggly.
  • Turn off the oven and let the cheesecake cool inside with the door slightly open for 1 hour.

6. Chill and Serve

  • Refrigerate for at least 4 hours or overnight.
  • Run a knife around the edge before releasing the springform pan.
  • Flip onto a serving plate so the pineapple side is on top.
  • Slice and enjoy!

Tips for the Best Pineapple Right Side Up Cheesecake

  • Use room temperature ingredients – This ensures a smooth, lump-free batter.
  • Avoid overmixing – Overmixing can incorporate too much air, leading to cracks.
  • Water bath for even baking – Place a pan of hot water on the lower oven rack to create steam.
  • Chill thoroughly – A properly chilled cheesecake is firm and flavorful.

Frequently Asked Questions

1. Can I use fresh pineapple instead of canned?

Yes! If using fresh pineapple, cook the slices in butter and brown sugar for a few minutes to soften them.

2. How do I store leftovers?

Store in an airtight container in the refrigerator for up to 5 days.

3. Can I freeze this cheesecake?

Yes! Wrap slices tightly in plastic wrap and store in a freezer-safe container for up to 3 months.

4. What if my cheesecake cracks?

No worries! Cover any cracks with whipped cream or extra pineapple slices.

5. Can I make this cheesecake without a springform pan?

A deep cake pan can work, but lining it with parchment paper helps with flipping.

Conclusion

This Pineapple Right Side Up Cheesecake is a delightful combination of classic cheesecake and tropical pineapple upside-down cake. With its buttery crust, caramelized pineapple topping, and creamy filling, it’s sure to become a favorite in your dessert repertoire. Whether you’re making it for a special occasion or just because, this cheesecake is guaranteed to impress!

Try it today and let the tropical flavors transport you to paradise! 🍍🍒

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