Pineapple Upside Down Cake: Retro Charm for Parents’ Day Celebration

Here’s how to make a pineapple upside down cake that’s simple, rustic and delicious, and perfect to serve for Parents’ Day.

Some desserts never go out of style, and the pineapple upside down cake is a prime example. With its buttery caramelised pineapple rings, ruby red cherries, and soft vanilla cake, this vintage beauty brings color, flavor, and nostalgia to the table. A delightful showstopper and a delicious bite, it’s the perfect treat to honor your parents on Parents’ Day. This recipe walks you through every step to create a moist, golden cake with perfectly glazed fruit on top. So let’s dive into this charming retro dessert that’s as delightful to make as it is to eat.

Ingredients:

¼ cup (60 g) unsalted butter
½ cup (100 g) light brown sugar
8 pineapple slices (canned or fresh, drained)
Maraschino cherries or glazed cherries (optional, for garnish)
1½ cups (190 g) all purpose flour
1½ tsp baking powder
¼ tsp salt
½ cup (120 ml) milk (room temperature)
¼ cup (60 ml) pineapple juice (from the canned pineapple) or fresh juice
1 tsp vanilla extract
½ cup (115 g) unsalted butter (softened)
¾ cup (150 g) granulated sugar
2 large eggs (room temperature)

Method:

In a small saucepan over low heat, melt ¼ cup butter and stir in the brown sugar. Cook for 2 minutes until the sugar is dissolved and the mixture is bubbling. Pour this caramel mixture into the bottom of your greased cake pan. Swirl the pan gently to ensure the entire bottom is coated evenly.
Arrange the pineapple slices on top of the brown sugar mixture. You can fit around 7 in a circular pattern and one in the center. Place a cherry in the middle of each ring, if using. Set aside.
Preheat your oven to 175°C or 350°F. This allows the cake to bake evenly from the moment it goes in.
In a medium bowl, sift together the flour, baking powder, and salt. Set aside.
In a small bowl or jug, mix together the milk, pineapple juice, and vanilla extract. These ingredients help add moisture and subtle tang to the cake.
In a large mixing bowl, beat ½ cup softened butter and granulated sugar together until light and fluffy. This should take about 3 minutes with an electric mixer. This creaming step incorporates air into the batter for a lighter texture.
Beat in the eggs one at a time, mixing well after each addition. Scrape down the sides of the bowl to ensure everything is well combined.
Add the flour mixture in three parts, alternating with the milk mixture in two parts. Begin and end with the dry ingredients. Mix on low speed or gently fold by hand until just combined. Do not overmix, or the cake may turn out dense.
Carefully spoon the batter over the pineapple and cherries in the pan. Smooth the surface with a spatula. Make sure not to disturb the arranged fruit.
Place the cake in the centre of the preheated oven and bake for 45 minutes, or until a toothpick inserted into the centre comes out clean and the top is golden. If the cake begins to brown too quickly, cover loosely with foil during the last 10 minutes of baking.
Let the cake rest in the pan for about 15 minutes after removing it from the oven. Do not let it cool completely in the pan or the topping may stick.
Run a knife gently around the edges to loosen. Place a plate or serving dish upside down over the cake pan. Holding both the pan and the plate, carefully flip them over in one swift motion. Lift the pan slowly to reveal the glossy pineapple topping. If any fruit sticks to the pan, simply lift it off and place it back onto the cake. It will still look beautiful.
Serve slightly warm with whipped cream or vanilla ice cream. Sprinkle a bit of toasted coconut over the top for a tropical twist. Dust lightly with powdered sugar for a refined finish.
Store leftovers in an airtight container at room temperature for up to 2 days. Refrigerate for up to 5 days, bringing to room temperature or gently warming before serving. Freeze slices wrapped individually in plastic wrap and foil. Thaw and reheat before serving.