Best Pineapple Upside Down Cake Recipe with Cherries

A perfect mix of fluffy cake and sweet tropical fruit, pineapple upside-down cake is a scrumptious dessert any time of the year.

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I love pineapple. I love cake. Pineapple upside-down cake is the perfect mixture of both and oh so good! Especially when I make it with lots of extra pineapple chunks!

I can’t even remember the first time I had a classic pineapple upside-down cake, but it’s one of my favorites. If I had a choice of any fruit, it is always pineapple. Because of this, I sometimes make the cake with only pineapple instead of the little maraschino cherries. But, Justin likes the cherries so I will add a few for him.

Recently, I tried making this in a springform pan because it was the only one I had cleaned at the time. I do NOT suggest this! It made a mess of the oven because the butter and brown sugar started leaking out of the pan. I noticed quickly so I placed another pan underneath to catch the rest of the drippings. You can also make this in a cast iron skillet since those are sage for baking. 

The hardest part is always flipping the cake. There have been times that it doesn’t all release from the pan and I have pieced it back together. Most of the time, you can’t even tell! The sugar topping is what gets stuck. So as long as you get it quickly, you can usually place it back on top of the cake and it melts into the rest of the topping.

For this recipe, you’ll make a homemade cake batter. If you don’t have time, don’t have the basic ingredients, or prefer not to make it from scratch, you can purchase a box of yellow cake mix and use that instead. Prepare the box cake mix according to the directions and pour that over the pineapple. 

Simple Ingredients

Unsalted Butter-Melted

Melt butter to use as the base of the cake, which will eventually be flipped to be the sugar topping on the cake. 

Brown Sugar

The other key ingredient for the topping is brown sugar. It will melt nicely and give a caramelized look and taste to the cake. 

Pineapple Slices

If possible, buying fresh pineapple will always have a better taste. We like to buy a pineapple, cut it into whole rings, and then save the pineapple juice for use in other recipes such as a strawberry pineapple daiquiri. Otherwise, canned pineapple will work fine for this easy recipe.

Maraschino Cherries

The cherries add a small amount of flavor but look really nice on the finished cake. They add a pop of color that you wouldn’t otherwise have. 

All-Purpose Flour

The base of the cake is made with flour, like most cakes. I’ve only ever made this with all-purpose flour but would like to try it with whole wheat flour next time. Or, if you have cake flour, you can use that and omit the baking powder. 

​Granulated Sugar

Granulated sugar, or white sugar, is mixed into the cake to make sure it has a sweet taste. 

Baking Powder

The baking powder will help the cake rise. This is crucial, even at such a small amount. 

Milk

The milk helps to bring the batter together. You can use whole milk or a non-dairy milk. Or, for a more moist cake, replace the milk with sour cream. 

Unsalted Butter-Softened

Make sure your butter is softened so it combines properly with the other ingredients in the cake batter. 

Egg

I like to use a whole egg for this recipe. The yolk adds a bit of flavor and the white keeps it light and fluffy. For an even more fluffy cake, use two egg whites in place of one whole egg. 

​Vanilla Extract

I mean, is it even a cake if it doesn’t have vanilla extract? Adding a small amount of vanilla extract will bring out the delicious sweet taste of the cake. 

Pineapple Upside-Down Cake Step by Step

Ingredients

• 2 tbsp unsalted butter (melted)
• 1/3 cup brown sugar
• 8 oz can pineapple slices (drained and halved)
• 4 maraschino cherries (halved)
• 1 1/2 cups all-purpose flour
• 2/3 cup granulated sugar
• 2 tsp baking powder
• 2/3 cup milk
• 1/2 cup unsalted butter (softened to room temperature)
• 1 egg
• 1 tsp vanilla extract

Instructions

Preheat the oven to 350F, then melt the butter and pour it into the bottom of a 9-inch round cake pan. Stir in the brown sugar and water until it forms a paste that you can spread in the bottom of the pan.

Place the pineapple rings around the edges of the pan. Cut the cherries in half and place those inside each pineapple ring and in any other gaps you want to fill.

Cake

In a large bowl, whisk together the flour, sugar, and baking powder.

Add the milk, softened butter, egg, and vanilla extract. Use a whisk to thoroughly combine and form the cake batter.

Pour the cake batter gently over the pineapple and cherries until it covers everything. Level out with a rubber spatula as needed.

Bake for about 30-35 minutes, or until a toothpick inserted in the center comes out clean.

Let the cake cool on a wire rack for about 5 minutes. If the cake is not very flat, it may help to cut a small amount off to make it level. When you flip the cake, if the bottom is bowed, it may crack as it settles.

Carefully flip the cake upside down onto a serving platter. Cut and serve warm.

Pineapple Upside Down Cake Leftovers

Storage: Place leftover slices of pineapple cake in an airtight container or cover with plastic wrap. Refrigerate for 1-2 days. 

Reheating: The delicious cake doesn’t need to be warm, but it tastes better if you take the chill out. I like to warm it in the microwave for about 15 seconds. 

Recipe

Pineapple Upside Down Cake

A perfect mix of fluffy cake and sweet tropical fruit, pineapple upside down cake is a scrumptious dessert any time of the year.

Prep Time 30 minutes minutes

Cook Time 30 minutes minutes

Total Time 1 hour hour

Course:

Dessert

Cuisine:

American

Diet

Vegetarian

Keyword:

cake

|

pineapple

Dietary Needs:

Nut-Free

Servings: 8 pieces

5 from 7 votes

Ingredients

• 2 tbsp unsalted butter (melted)
• 1/3 cup brown sugar
• 8 oz can pineapple slices (drained and halved)
• 4 maraschino cherries (halved)
• 1 1/2 cups all-purpose flour
• 2/3 cup granulated sugar
• 2 tsp baking powder
• 2/3 cup milk
• 1/2 cup unsalted butter (softened)
• 1 egg
• 1 tsp vanilla extract

Recommended Equipment

• Round Cake Pans – 9 inch
• Mixing Bowls – Stainless Steel
• Electric Mixer
• Wire Cooling Rack

Instructions

• Preheat oven to 350F
• Put melted butter in a 9-inch round cake pan
• Stir in brown sugar and 1 tbsp water
• Arrange pineapple and cherries in the pan and set aside
• In a medium bowl stir together flour, sugar, and baking powder
• Add milk, softened butter, egg, and vanilla
• Beat with electric mixer on low speed until combined
• Spoon batter over fruit
• Bake for 30-35 minutes or until toothpick comes out clean
• Cool on wire rack for 5 minutes
• Loosen from cake pan and invert on a plate and serve warm

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Nutrition Facts

Pineapple Upside Down Cake

Amount Per Serving (1 piece)

Calories 355 Calories from Fat 135

% Daily Value*

Fat 15g23%

Saturated Fat 9g45%

Cholesterol 60mg20%

Sodium 147mg6%

Potassium 233mg7%

Carbohydrates 50g17%

Fiber 1g4%

Sugar 31g34%

Protein 4g8%

Vitamin A 520IU10%

Vitamin C 2.6mg3%

Calcium 101mg10%

Iron 1.4mg8%

* Percent Daily Values are based on a 2000 calorie diet.

All nutritional information is based on third-party calculations and should be considered estimates. Actual nutrition content will vary based on brands used, measuring methods, portion sizes, and more.

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