Tropical Individual Caramelized Desserts

This mini pineapple upside down cake recipe transforms a classic dessert into charming individual portions that capture all the caramelized goodness of the original. Each bite delivers the perfect balance of buttery cake, sweet caramelized pineapple, and that signature maraschino cherry on top.

I first made these for my daughter's birthday when she requested "something with pineapple," and they've become our go-to impressive-but-easy dessert for family gatherings. The looks on guests' faces when they see these miniature versions of the classic cake is priceless every time.

Ingredients

• Unsalted butter: creates that rich caramel topping that makes this dessert irresistible
• Brown sugar: combines with butter for that signature caramelized flavor essential to upside down cakes
• Canned pineapple slices: save time and provide consistent results look for ones packed in juice rather than syrup
• Maraschino cherries: add that classic pop of color and sweet flavor select jars with natural coloring if possible
• All-purpose flour: forms the foundation of our tender cake batter
• Baking powder: ensures the perfect rise in our cake
• Salt: enhances all the flavors and balances the sweetness
• Granulated sugar: adds the right level of sweetness to the cake batter
• Egg: binds the ingredients and adds structure to the cake
• Milk: moistens the batter and creates a tender crumb whole milk works best
• Vanilla extract: adds warmth and depth use pure extract for the best flavor

Step-by-Step Instructions

Prepare the pan and oven:

Preheat your oven to a moderate 350°F which ensures even baking without browning too quickly. Thoroughly grease each cup of your muffin tin, making sure to coat the sides completely to prevent sticking. A light coating of flour after greasing can provide extra insurance against sticking.

Create the caramel base:

Melt the butter in a small saucepan over medium-low heat until completely liquid but not browning. Add the brown sugar and stir constantly until the mixture becomes smooth and slightly thickened, about 2 minutes. The sugar should be completely dissolved. Carefully spoon this hot mixture into the bottom of each muffin cup, dividing equally.

Arrange the fruit:

Place one pineapple slice into each muffin cup, pressing gently into the caramel mixture. The pineapple may need to be trimmed slightly to fit perfectly in standard muffin cups. Position a bright red maraschino cherry in the center hole of each pineapple slice, pressing lightly to secure it in the caramel.

Mix the wet ingredients:

In a medium bowl, use an electric mixer to cream together the granulated sugar and egg until the mixture becomes pale and fluffy, about 2 minutes. This incorporates air into the batter for a lighter texture. Add the milk and vanilla extract and mix until fully incorporated.

Combine the dry ingredients:

In a separate bowl, whisk together the flour, baking powder, and salt until evenly distributed. This ensures the leavening agent is evenly dispersed throughout the batter for consistent rising.

Complete the batter:

Gradually add the dry ingredient mixture to the wet ingredients, mixing on low speed just until combined. Avoid overmixing which can develop gluten and create a tough cake. The batter should be smooth but not beaten excessively.

Fill the cups and bake:

Carefully spoon the batter over the pineapple and caramel in each muffin cup, filling each about three-quarters full. The batter will rise during baking. Place in the preheated oven and bake for exactly 20 minutes, or until a toothpick inserted into the center of a cake comes out clean with no wet batter.

Save

My favorite part of making these cakes is the magical moment of turning them out of the pan. I remember the first time I made them with my grandmother, who taught me to let them cool for exactly five minutes before inverting them onto the serving plate. Too soon and they fall apart, too late and the caramel hardens, making them stick to the pan. That precise timing is a kitchen lesson I've carried with me for decades.

Storing Your Mini Cakes

These mini pineapple upside down cakes stay fresh at room temperature for about 2 days when stored in an airtight container. For longer storage, refrigerate them for up to 5 days, though the texture is best within the first 48 hours. To reheat, warm them in the microwave for 15-20 seconds or in a 300°F oven for about 5 minutes until just warm. The gentle heat will revive the caramel topping and make them taste freshly baked.

Creative Variations

While the classic pineapple and cherry combination is timeless, these mini cakes welcome creative adaptations. Try using peach slices with a sprinkle of cinnamon for a southern twist, or apple slices with caramel for a fall-inspired version. For an adult dessert, consider soaking the fruit in rum before arranging in the pan. You can also experiment with adding coconut flakes to the batter or sprinkling chopped nuts into the caramel layer before adding the fruit.

Serving Suggestions

Elevate these mini cakes by serving them with a scoop of vanilla ice cream or a dollop of lightly sweetened whipped cream. The contrast between the warm cake and cold topping is delightful. For a brunch setting, pair them with coffee or a tropical mimosa. During the holidays, a light dusting of powdered sugar and a sprig of mint turns these into festive treats that brighten any dessert table.

The History Behind the Dessert

Pineapple upside down cake gained popularity in America during the 1920s after Dole Pineapple Company held a recipe contest featuring canned pineapples. The concept of cooking fruit at the bottom of a cake pan dates back centuries to skillet cakes cooked over open fires. These mini versions maintain that nostalgic appeal while updating the presentation for modern entertaining. The individual portions also cook more quickly and evenly than a full-sized cake, ensuring perfect results every time.

Recipe FAQs

→ Can I use fresh pineapple instead of canned?

Yes, you can substitute fresh pineapple for canned. Cut fresh pineapple into rings or chunks that fit your muffin cups. Keep in mind that fresh pineapple won't be as sweet as canned, so you might want to increase the brown sugar slightly or macerate the fresh pineapple in a bit of sugar before using.

→ How do I prevent the cakes from sticking to the pan?

Ensure your muffin tin is well-greased with butter or cooking spray. Allow the cakes to cool for about 5 minutes after baking (not longer, as the sugar will harden), then run a knife around the edges before inverting onto a serving plate. The butter-sugar mixture helps create a non-stick surface when properly prepared.

→ Can these mini cakes be made in advance?

Yes, you can make these up to a day ahead. After cooling completely, store them in an airtight container at room temperature. To refresh before serving, warm them briefly in the microwave for 10-15 seconds. For longer storage, refrigerate for up to 3 days or freeze for up to 3 months.

→ What can I use instead of maraschino cherries?

If you prefer alternatives to maraschino cherries, try fresh or frozen cherries, raspberries, blueberries, or even small pieces of strawberry. For a different flavor profile, consider pecan halves, small pieces of mango, or even caramelized banana slices.

→ Can I make these in a different size pan?

Absolutely! This recipe adapts well to different pans. For mini versions, use mini muffin tins and cut pineapple into small pieces. For larger servings, use a jumbo muffin tin or ramekins. You can even make a single cake in an 8-inch cake pan, though baking time will increase to approximately 30-35 minutes.

→ Are these mini cakes gluten-free?

The standard recipe is not gluten-free due to the all-purpose flour. However, you can easily adapt it using a 1:1 gluten-free flour blend designed for baking. The other ingredients (pineapple, cherries, butter, sugar) are naturally gluten-free, but always check packaged ingredients for cross-contamination if serving to someone with celiac disease.