This Classic Pineapple Upside Down Cake is a showstopper dessert that brings back warm, nostalgic memories with every buttery bite. It’s a timeless beauty topped with caramelized pineapple rings and glowing maraschino cherries, all layered over a soft, tender vanilla cake. The moment it flips out of the pan, revealing its glossy golden crown, you’ll know why it’s been a favorite for generations.

Whether you’re hosting a weekend gathering or simply craving something sweet and retro, this cake delivers every single time. It’s moist, flavorful, and surprisingly simple to make. With its irresistible topping and cozy cake base, it’s no wonder this recipe never goes out of style.

Why You’ll Love This Classic Pineapple Upside Down Cake

This cake combines the ease of a one-layer bake with the elegance of a dramatic presentation. The brown sugar glaze creates a sticky, sweet topping that melds perfectly with the pineapple. The cake itself is buttery, soft, and light, creating that ideal contrast. Best of all, it requires minimal decorating effort since the top becomes picture-perfect as soon as you turn it out.

What Kind of Pineapple Should I Use?

Canned pineapple rings are your best friend for this recipe. They’re consistent in size, sweet, and easy to arrange. Choose rings packed in juice rather than syrup for a more balanced flavor. Fresh pineapple can also work, but be sure to slice it thin enough to cook evenly and release its juices during baking.

Ingredients for the Classic Pineapple Upside Down Cake

The beauty of this cake is in its simplicity. With just a handful of pantry staples and a can of pineapple, you can make something that tastes bakery-fancy.

Pineapple rings add the signature tang and tropical sweetness, as well as the stunning pattern on top of the cake.

Maraschino cherries bring that pop of color and a hint of almond-like sweetness that’s hard to resist.

Brown sugar is used to caramelize the fruit, adding a deep molasses flavor and a sticky glaze.

Unsalted butter gives richness to both the caramel base and the cake itself.

All-purpose flour forms the backbone of the cake batter, giving it structure and softness.

Granulated sugar sweetens the cake without overpowering the fruit topping.

Eggs bind everything together and provide a light, fluffy texture.

Baking powder helps the cake rise to the perfect height.

Salt enhances all the sweet and fruity flavors.

Milk moistens the batter for a smooth consistency and tender crumb.

Vanilla extract rounds out the flavor with warmth and depth.

How To Make the Classic Pineapple Upside Down Cake

Step 1: Prepare the Pan

Preheat your oven to 350°F. In a 9-inch round cake pan, melt 1/4 cup butter and sprinkle 1/2 cup brown sugar evenly over the base. Arrange pineapple rings over the sugar, placing a maraschino cherry in the center of each.

Step 2: Make the Batter

In a bowl, whisk together 1 1/2 cups flour, 1 tsp baking powder, and 1/4 tsp salt. In a separate bowl, beat 1/2 cup softened butter with 1 cup granulated sugar until light and fluffy. Add 2 eggs, one at a time, then mix in 1 tsp vanilla.

Gradually add the dry ingredients, alternating with 1/2 cup milk, beginning and ending with the dry mix. Beat just until combined.

Step 3: Assemble and Bake

Pour the batter over the arranged pineapple rings and smooth the top. Bake for 45 to 50 minutes, or until a toothpick inserted comes out clean. Let cool in the pan for 10 minutes.

Step 4: Flip and Reveal

Place a plate over the cake pan and invert quickly. Lift the pan carefully to reveal the glistening pineapple design. Let cool before slicing.

How to Serve and Store This Cake

This recipe serves about 8 generous slices, perfect for family desserts or dinner parties. It’s best enjoyed slightly warm or at room temperature. A scoop of vanilla ice cream on the side makes it feel extra special.

To store, wrap leftovers in plastic wrap or place in an airtight container. It will keep at room temperature for up to 2 days or refrigerated for up to 5. You can also freeze individual slices for a quick treat later—just reheat gently.

What to Serve With Classic Pineapple Upside Down Cake?

Vanilla Ice Cream

A chilled scoop melts into the warm cake, creating an ultra-comforting dessert combo.

Coconut Whipped Cream

For a tropical twist, add a dollop of lightly sweetened coconut cream.

Spiced Chai Tea

The spices complement the brown sugar and pineapple beautifully.

Grilled Pineapple

Double down on the pineapple flavor by serving some grilled slices alongside the cake.

Salted Caramel Sauce

A drizzle of caramel enhances the already rich glaze and takes it to indulgent heights.

Fresh Mint

Add a sprig for a refreshing, fragrant garnish that brightens the plate.

Coffee or Espresso

Perfect for an afternoon treat, this cake pairs wonderfully with a bold coffee.

Want More Cake Ideas with a Twist?

If you adore this retro gem, you’ll love exploring these other dessert creations:

• Try the Old-Time Oven Peach Cobbler for a sweet Southern classic.

• Make a batch of Ooey Gooey Bars that offer sticky, buttery bliss in every bite.

• Or for citrus lovers, the Delicious Lemon Cake to Die For will bring tangy joy.

• Want a playful cookie version? Check out Cherry-Topped Coconut Macaroons for chewy, tropical treats.

• And don’t miss the Mini Cinnamon Roll Cheesecakes for a swirl of cream cheese magic.

Save This Recipe For Later

📌 Save this recipe to your Pinterest dessert board so you can come back to it any time.

And let me know in the comments how yours turned out. Did you try it with fresh pineapple or stick to canned? Did you sneak in a splash of rum?

I love hearing how others bring their own twist to classics like this. Your tips and questions are always welcome.

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