When you think of pineapple upside down treats, the classic cake likely comes to mind, but there's so much more to investigate. You might find yourself intrigued by individual cupcakes that make entertaining effortless or a vegan version that caters to dietary preferences. Perhaps you've never considered starting your day with pineapple upside down pancakes, or you're curious about a tart that enhances the dessert experience. Each recipe offers a unique spin on a beloved favorite, and you might just discover a new favorite among them. So, which one will you try first?
Classic Pineapple Upside Down Cake

Pineapple Upside Down Cake is a delightful dessert that brings a touch of nostalgia with its caramelized pineapple and buttery cake base. This classic recipe isn't only easy to make but also a showstopper when served.
The combination of sweet, juicy pineapples and the rich, moist cake creates a harmonious blend of flavors that will surely impress your family and friends. Perfect for any occasion, this cake is a must-try for anyone looking to indulge in a slice of paradise.
Ingredients:
- 1/4 cup unsalted butter
- 1 cup packed brown sugar
- 1 can (20 oz) sliced pineapple, drained
- Maraschino cherries (optional)
- 1 1/2 cups all-purpose flour
- 1 cup granulated sugar
- 1/2 cup unsalted butter, softened
- 2 large eggs
- 1 teaspoon vanilla extract
- 1/2 teaspoon baking powder
- 1/2 teaspoon baking soda
- 1/2 teaspoon salt
- 1/2 cup buttermilk
Cooking Instructions:
Preheat your oven to 350°F (175°C). In a 9-inch round cake pan, melt 1/4 cup of butter in the oven, then sprinkle the brown sugar evenly over the melted butter.
Arrange the pineapple slices on top of the sugar and place a maraschino cherry in the center of each pineapple slice if desired. In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
Add the eggs one at a time, mixing well after each addition, then stir in the vanilla. In another bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, alternating with the buttermilk, until just combined.
Pour the batter over the pineapple layer in the pan and smooth it out. Bake for 40-45 minutes, or until a toothpick inserted in the center comes out clean. Allow the cake to cool for about 10 minutes before inverting it onto a serving plate.
Extra Tips:
For an extra burst of flavor, consider adding a pinch of cinnamon to the batter or using fresh pineapple instead of canned.
Make sure to let the cake cool slightly before flipping it to prevent the pineapples from sticking. If you're feeling adventurous, you can also experiment with other fruit toppings like peaches or cherries for a different twist on the classic recipe.
Enjoy your delicious Pineapple Upside Down Cake with a scoop of vanilla ice cream for an indulgent treat!
Pineapple Upside Down Cupcakes

Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert, offering individual servings that are both fun and easy to make. These mini cakes are topped with sweet caramelized pineapple and a cherry, creating a perfect balance of flavors.
Ideal for parties or as a treat for yourself, these cupcakes are sure to impress anyone with their charming presentation and delicious taste.
Ingredients:
- 1/2 cup unsalted butter, melted
- 1 cup brown sugar, packed
- 1 can (20 oz) pineapple slices, drained
- Maraschino cherries
- 1 cup all-purpose flour
- 1 teaspoon baking powder
- 1/2 teaspoon salt
- 1/2 cup granulated sugar
- 1 large egg
- 1/2 cup milk
- 1 teaspoon vanilla extract
Instructions:
Preheat your oven to 350°F (175°C) and line a muffin tin with cupcake liners. In a small bowl, combine the melted butter and brown sugar, then evenly distribute the mixture into the bottom of each cupcake liner.
Place a pineapple slice on top of the sugar mixture, and add a cherry in the center of each pineapple slice. In a separate bowl, whisk together the flour, baking powder, and salt.
In another bowl, beat the granulated sugar, egg, milk, and vanilla extract until well combined. Gradually add the dry ingredients to the wet mixture, stirring until just combined.
Pour the batter over the pineapple and cherry layer in each liner, filling them about two-thirds full. Bake for 20-25 minutes or until a toothpick inserted in the center comes out clean.
Allow the cupcakes to cool for a few minutes before inverting them onto a serving platter.
Extra Tips:
For the best results, verify that the pineapple slices are well-drained to prevent excess moisture from affecting the batter.
You can also experiment with different toppings, such as toasted coconut or pecans, to add extra flavor and texture. If you want to make these cupcakes ahead of time, they can be stored in an airtight container for up to three days, but they're best enjoyed fresh out of the oven.
Additionally, feel free to substitute the cherries with other fruits like blueberries or strawberries for a unique twist!
Vegan Pineapple Upside Down Cake

Vegan Pineapple Upside Down Cake is a delicious twist on the classic dessert that showcases the sweet, caramelized pineapple topped with a moist and flavorful cake, all without any animal products. Perfect for special occasions or a delightful treat for any day, this cake is sure to impress both vegans and non-vegans alike.
With its beautiful presentation and rich flavors, it's a fantastic dessert that balances the tartness of pineapple with the sweetness of sugar and a hint of vanilla.
Ingredients:
- 1 cup brown sugar
- 1/4 cup vegan butter, melted
- 1 can (about 20 ounces) sliced pineapple in juice, drained
- Maraschino cherries (optional)
- 1 1/2 cups all-purpose flour
- 1 cup almond milk (or any plant-based milk)
- 1/3 cup vegetable oil
- 1/2 cup granulated sugar
- 1 tablespoon apple cider vinegar
- 1 teaspoon vanilla extract
- 1 teaspoon baking powder
- 1/2 teaspoon baking soda
- 1/4 teaspoon salt
Instructions:
Preheat your oven to 350°F (175°C) and grease a 9-inch round cake pan. In a small bowl, mix together the brown sugar and melted vegan butter until well combined, then spread this mixture evenly across the bottom of the prepared pan.
Arrange the drained pineapple slices over the sugar mixture and place a maraschino cherry in the center of each pineapple slice if using.
In a large mixing bowl, whisk together the flour, granulated sugar, baking powder, baking soda, and salt. In another bowl, combine the almond milk, vegetable oil, apple cider vinegar, and vanilla extract.
Pour the wet ingredients into the dry ingredients and mix until just combined. Carefully pour the batter over the pineapple layer in the cake pan.
Bake for 30-35 minutes, or until a toothpick inserted into the center comes out clean. Allow the cake to cool for about 10 minutes before inverting it onto a serving plate.
Extra Tips:
For the best results, verify all your ingredients are at room temperature before mixing, as this helps create a lighter cake.
You can also experiment with adding spices like cinnamon or nutmeg to the batter for added flavor. If you prefer a more tropical taste, consider adding shredded coconut or using coconut milk instead of almond milk.
Finally, to make the cake even more visually appealing, feel free to garnish it with chopped nuts or additional fruit slices when serving. Enjoy your delightful Vegan Pineapple Upside Down Cake!
Pineapple Upside Down Pancakes

Pineapple Upside Down Pancakes are a delightful twist on the classic dessert, transforming it into a breakfast favorite.
These fluffy pancakes are topped with caramelized pineapple and cherries, creating a sweet and tangy flavor that's sure to brighten your morning. Perfect for a weekend brunch or a special occasion, these pancakes aren't only delicious but also visually impressive, making them a great way to start the day with a tropical flair.
Ingredients:
- 1 cup all-purpose flour
- 2 tablespoons sugar
- 1 teaspoon baking powder
- 1/2 teaspoon baking soda
- 1/4 teaspoon salt
- 1 cup buttermilk
- 1 large egg
- 2 tablespoons melted butter
- 1 cup crushed pineapple, drained
- 1/2 cup maraschino cherries
- 1/4 cup brown sugar
- 1 tablespoon butter (for caramelizing)
Cooking Instructions:
In a large mixing bowl, whisk together the flour, sugar, baking powder, baking soda, and salt.
In another bowl, combine the buttermilk, egg, and melted butter, then mix until well blended.
Pour the wet ingredients into the dry ingredients and stir until just combined; be careful not to overmix.
In a skillet over medium heat, melt 1 tablespoon of butter, then sprinkle the brown sugar evenly over the skillet.
Add the crushed pineapple and maraschino cherries to the skillet and cook for 2-3 minutes until caramelized.
Pour the pancake batter over the pineapple mixture, cooking until bubbles form on the surface, then flip and cook until golden brown.
Repeat with the remaining batter.
Extra Tips:
For the best results, make sure your skillet is preheated and well-greased to prevent sticking.
You can also customize your pancakes by adding chopped pecans or walnuts to the batter for added crunch.
If you like a sweeter pancake, feel free to drizzle some maple syrup on top before serving.
And for a fun twist, try using fresh pineapple instead of canned for a more vibrant flavor!
Tropical Pineapple Upside Down Tart

Tropical Pineapple Upside Down Tart is a delightful twist on the classic dessert, combining buttery pastry with sweet, caramelized pineapples and a hint of tropical flavor from coconut.
This tart not only looks stunning when inverted but also delivers a burst of flavor with every bite. Perfect for a summer gathering or a cozy family dinner, this recipe is sure to impress and satisfy your sweet tooth.
Ingredients:
- 1 pre-made pie crust
- 1 can (20 oz) pineapple slices, drained
- 1/2 cup unsalted butter
- 1 cup brown sugar
- 1/2 cup shredded coconut
- 1/4 cup maraschino cherries
- 1 tsp vanilla extract
- 1/2 tsp ground cinnamon
- 1/4 tsp salt
- Optional: whipped cream for serving
Instructions:
Preheat your oven to 350°F (175°C).
In a medium saucepan, melt the butter over medium heat and stir in the brown sugar, cinnamon, and salt until well combined.
Once the mixture is bubbling, remove it from the heat and pour it into a 9-inch tart pan, spreading it evenly.
Arrange the pineapple slices over the brown sugar mixture, and place a maraschino cherry in the center of each slice.
Sprinkle the shredded coconut over the pineapples, then carefully lay the pie crust over the top, tucking the edges down around the fruit.
Bake for 30-35 minutes, or until the crust is golden brown.
Allow the tart to cool for 10 minutes before inverting it onto a serving platter.
Extra Tips:
For an added tropical touch, consider using fresh pineapple instead of canned, as it will provide a firmer texture and brighter flavor.
If you enjoy a more caramelized topping, you can broil the tart for an additional 2-3 minutes after baking.
Make sure to let the tart cool slightly before inverting to prevent the caramel from spilling out.
Serve with a dollop of whipped cream or a scoop of vanilla ice cream for a delightful contrast to the warm tart.