Pineapple Right Side Up Cheesecake

Escape to a tropical paradise with every decadent bite of our Pineapple Right Side Up Cheesecake! Combining the lusciousness of cheesecake with the tropical sweetness of pineapple and the nostalgic charm of a classic upside-down cake, this dessert is sure to transport you to sunny shores and swaying palm trees. Whether you’re hosting a summer soirée or simply craving a taste of the tropics, this recipe promises to delight your taste buds and leave you craving more. Let’s dive into the delicious details of this irresistible treat.


Graham Cracker Crust:

  • 1 ¼ cups graham cracker crumbs
  • 46 grams brown sugar
  • 42 grams sugar
  • 6-7 tablespoons melted butter (add slowly, may not need all)


  • 16 ounces cream cheese, room temperature
  • 80 grams sour cream, room temperature
  • 1 tablespoon heavy cream, room temperature
  • 1 tablespoon vanilla extract
  • 140 grams granulated sugar
  • 2 tablespoons cornstarch
  • 2 eggs, room temperature
  • 25 maraschino cherries, cut in half
  • 4 slices canned pineapple, cut into chunks


  • Whipped cream
  • Pineapple slices (use the rest from 1 can, cut in half)
  • Cherries with stems


  1. Crust: Preheat oven to 300°F (149°C). Spray a 6×3-inch removable bottom pan with non-stick spray, line with parchment, and spray again. Mix crust ingredients and press into pan. Bake 10-12 minutes. Cool on a rack over a jellyroll pan.
  2. Cheesecake: Beat cream cheese until creamy, about 4-5 minutes, scraping the bowl a few times. Mix in sour cream, heavy cream, vanilla, sugar, and cornstarch until smooth. Add eggs gently, then fold in cherries and pineapple. Pour into crust. Bake at 300°F for 12 minutes, then at 225°F for 95 minutes without opening the oven. Leave in the off oven for 1 hour, then crack open the oven for another hour. Cool on a rack, then chill overnight. Remove from pan, place on cake plate, and garnish.

Nutritional Information:

  • Prep Time: 30 minutes
  • Cooking Time: 107 minutes
  • Total Time: 24 hours
  • Calories: 500 per serving
  • Servings: 8

Serving Tips:

  1. For a stunning presentation, top each slice of Pineapple Right Side Up Cheesecake with a dollop of whipped cream and a pineapple slice, garnished with a cherry on top. This adds a delightful burst of color and flavor to each serving.
  2. Pair this tropical dessert with a scoop of coconut or vanilla ice cream for an extra indulgent treat. The creamy texture of the ice cream complements the richness of the cheesecake perfectly.
  3. To enhance the tropical theme, serve the cheesecake alongside a refreshing piña colada or a tropical fruit salad. The combination of flavors will transport your taste buds to a beachside paradise.
  4. Enjoy this cheesecake chilled for the best texture and flavor. Allow it to sit at room temperature for a few minutes before serving to soften slightly and bring out the full range of flavors.

Storage Tips:

  1. Store any leftover Pineapple Right Side Up Cheesecake in an airtight container in the refrigerator for up to 3-4 days. Make sure to cover it well to prevent any odors from permeating the dessert.
  2. To maintain the cheesecake’s freshness and prevent it from drying out, consider wrapping individual slices in plastic wrap before refrigerating them. This will help preserve their moisture and flavor.
  3. Avoid storing the cheesecake in the freezer, as this can alter its texture and affect the overall quality. Cheesecake tends to become grainy and lose its creamy consistency when frozen.
  4. If you need to transport the cheesecake, place it in a sturdy cake carrier or container to prevent it from getting damaged or squished during transit. Keep it chilled with ice packs or in a cooler to maintain its freshness.

By following these serving and storage tips, you can ensure that your Pineapple Right Side Up Cheesecake stays fresh, delicious, and ready to delight your taste buds whenever you crave a taste of the tropics.



  1. Tropical Twist: Add shredded coconut to the graham cracker crust for an extra layer of tropical flavor. You can also sprinkle coconut flakes on top of the cheesecake before serving for a decorative touch.
  2. Rum Infusion: For an adult twist, add a splash of rum to the cheesecake batter before baking. The rum adds a subtle boozy flavor that complements the tropical pineapple and cherry perfectly.
  3. Mango Madness: Substitute mango chunks for the pineapple in the cheesecake batter for a deliciously fruity variation. Top the cheesecake with fresh mango slices or a mango coulis for a burst of tropical flavor.
  4. Pineapple Upside Down Bars: Turn this cheesecake into portable bars by baking the crust and cheesecake filling in a square baking dish. Once cooled, cut into bars and top each with a slice of pineapple and a cherry for a fun twist on the classic dessert.
  5. Mini Cheesecake Bites: Make individual mini cheesecakes by using a mini muffin tin instead of a large pan. Press the graham cracker crust into the bottom of each muffin cup, fill with cheesecake batter, and bake until set. Top each mini cheesecake with a pineapple chunk and cherry for a bite-sized treat.
  6. Citrus Zest: Add a pop of citrus flavor by stirring in some lemon or lime zest into the cheesecake batter. The bright, tangy notes complement the sweetness of the pineapple and cherries beautifully.
  7. Nutty Crunch: Incorporate chopped macadamia nuts or almonds into the graham cracker crust for added texture and flavor. The nuttiness adds a delicious contrast to the creamy cheesecake and tropical fruits.


  1. Can I use fresh pineapple instead of canned pineapple? Yes, you can substitute fresh pineapple for canned pineapple in this recipe. Simply cut the fresh pineapple into chunks and use them as directed in the recipe.
  2. Can I make this cheesecake ahead of time? Absolutely! This cheesecake can be made a day or two in advance and stored in the refrigerator until ready to serve. In fact, it often tastes even better after chilling overnight, allowing the flavors to meld together.
  3. Can I use a different type of crust? While graham cracker crust is traditional for cheesecakes, you can certainly experiment with different crusts if you prefer. Try using crushed vanilla wafers, chocolate cookies, or even a gluten-free alternative like almond meal.
  4. How do I prevent cracks from forming on the surface of the cheesecake? To prevent cracks, it’s important to avoid overmixing the batter and to bake the cheesecake in a water bath. Additionally, following the recommended baking and cooling times in the recipe will help prevent cracks from forming.
  5. Can I freeze leftover cheesecake? While cheesecake can be frozen, it’s best to do so before adding any garnishes or toppings. Wrap the cheesecake tightly in plastic wrap and aluminum foil before freezing, and thaw it in the refrigerator overnight before serving.
  6. Can I omit the cherries from the recipe? Yes, you can omit the cherries if you prefer. The cheesecake will still be delicious without them, or you can substitute them with another fruit of your choice, such as strawberries or blueberries.
  7. Can I use a different type of fruit topping? Absolutely! Feel free to get creative with the fruit topping. Try using fresh berries, sliced peaches, or even a tropical fruit salsa for a different flavor profile.

With its irresistible combination of creamy cheesecake, tangy pineapple, and sweet cherries, our Pineapple Right Side Up Cheesecake is the ultimate dessert indulgence. Whether you’re celebrating a special occasion or simply treating yourself to a taste of the tropics, this recipe is guaranteed to satisfy your sweet tooth and leave you dreaming of sunny days ahead. So why wait? Whip up a batch today and let your taste buds take a trip to paradise!