Name: Best Pineapple Upside Down Cake
Prep time: 20 min
Cook time: 50 min
Total time: 70 min
Ingredients: 1 cup Butter, divided (1/2 cup for caramel and 1/2 cup softened for batter); 1.25 cups Dark Brown Sugar (For caramel and batter); 2 cans Sliced Pineapple in Juice, drained (Reserve juice for batter); 10-13 pieces Maraschino Cherries, stems removed (For topping); 2 cups All-Purpose Flour; 2 teaspoons Baking Powder; 0.5 teaspoons Salt; 0.5 cup Granulated Sugar; 2 large Eggs, at room temperature; 0.5 cup Whole Milk; 0.5 cup Reserved Pineapple Juice; 1 teaspoon Almond Extract (Can substitute with vanilla extract)

Jump to Recipe

Who can resist a slice of juicy, caramelized, golden Best Pineapple Upside Down Cake? It’s the ultimate comfort dessert—bursting with sweet pineapple flavor, luscious brown sugar, and that classic, sticky-sweet fruit topping that everyone secretly loves. Did you know this cake became popular in the 1920s thanks to a pineapple marketing campaign? It has stood the test of time, becoming a nostalgic favorite that impresses crowds and delights families today. I love how this cake comes together quickly with just a few pantry basics—it’s honestly easier than you think! If you’re a fan of my Classic Banana Bread, you’ll appreciate how this recipe marries traditional flavors with a showstopper presentation. Ready for a sweet treat that’s fuss-free and truly scrumptious? Let’s get baking!

What is Best Pineapple Upside Down Cake?

Why do we call it Pineapple Upside Down Cake? Well, have you ever baked something right-side up only to flip it over for a dramatic reveal? That’s exactly what happens here—and honestly, the upside-down magic never fails to wow both bakers and eaters! Legend has it, the way to a man’s heart is through his stomach, and I say, the way to anyone’s heart is with this cake. From the caramelized fruit to the golden crumb, this cake is a sweet surprise in every bite. Curious to see why generations have turned their cakes upside down? Bake along and watch the magic unfold in your own kitchen!

Why You’ll Love This

What makes Best Pineapple Upside Down Cake a home baker’s dream? First, it’s all about the glorious topping—juicy pineapple rings and vibrant maraschino cherries cozying up in a thick layer of buttery brown sugar caramel. Second, making this classic at home leaves store-bought versions in the dust and saves you a trip to the bakery (and some cash!). The flavor is unmatched—imagine moist, buttery cake crowned with gooey fruit that tastes like a tropical vacation. Plus, you can get creative with extra cherries or even a splash of rum. If you love my One Bowl Lemon Loaf, you’ll adore the similar simplicity and wow factor here. Try it—you’ll be hooked from the very first flip!

How to Make

Quick Overview

This Best Pineapple Upside Down Cake is easy enough for weeknights but impressive enough for celebrations. You’ll be amazed by how seamlessly the gooey brown sugar and pineapple topping transforms into a glossy, irresistible crown for your fluffy cake. The hands-on time is only about 20 minutes, and you’ll need just 45-50 minutes to bake. No fancy gadgets—just a bowl, a mixer, and a bit of joy in the kitchen!

Ingredients

1/2 cup butter
1 1/4 cups dark brown sugar
2 cans (20 oz each) sliced pineapple in juice, drained (reserve juice)
10-13 maraschino cherries, stems removed
2 cups all-purpose flour
2 teaspoons baking powder
1/2 teaspoon salt
1/2 cup butter, softened
1/2 cup granulated sugar
1/3 cup dark brown sugar
2 large eggs, at room temperature
1/2 cup whole milk
1/2 cup juice from the tinned pineapple
1 teaspoon almond extract

Directions

Preheat the oven to 350°F (175°C).
In a saucepan, melt 1/2 cup butter over medium heat. Stir in 1 1/4 cups dark brown sugar until dissolved and bubbly.
Pour this caramel mixture evenly into the bottom of a 9×13-inch baking dish.
Arrange the drained pineapple slices on top of the caramel. Place maraschino cherries in the center of each pineapple ring and anywhere else they fit for extra color and sweetness.
In a medium bowl, whisk together the flour, baking powder, and salt.
In a large bowl, cream together 1/2 cup softened butter, 1/2 cup granulated sugar, and 1/3 cup dark brown sugar until light and fluffy—about 2 minutes.
Add the eggs one at a time, beating well after each addition. Pour in the milk, 1/2 cup reserved pineapple juice, and almond extract. Mix until combined. Don’t worry if it looks slightly curdled—this is normal.
Gradually add the dry ingredients to the wet mixture, mixing just until smooth and no dry streaks remain.
Carefully spread the batter over the pineapple and cherries in the pan, smoothing the top with a spatula.
Bake for 45-50 minutes, or until a toothpick inserted into the center comes out clean and the top is golden brown.
Cool in the pan for just 5-10 minutes. Run a knife around the edges if needed, then invert the cake onto a large serving platter while it’s still warm. Serve slices while the caramel is gloriously gooey.

What to Serve With

Best Pineapple Upside Down Cake is a star on its own, but you can elevate your dessert menu by pairing it with some delicious sides. Try a scoop of classic vanilla ice cream or a dollop of freshly whipped cream for an extra creamy bite. For a summery twist, a light fruit salad with tropical fruits like mango and kiwi adds color and freshness. If you’re serving this after a special dinner, a simple cup of coffee, spice chai, or pineapple-mango iced tea will round off the flavors beautifully. Feel free to add toasted coconut flakes over your cake for an extra crunch!

Top Tips for Perfecting

Use dark brown sugar for extra caramel depth, but light brown sugar works if that’s all you have.
Drain your pineapple slices thoroughly so the cake doesn’t get soggy. You can even pat them dry with a paper towel.
Don’t forget to reserve some pineapple juice for the cake batter—it adds authentic fruitiness and stays true to the tropical flavor.
Want a little twist? Swap almond extract for vanilla or add a splash of spiced rum to the batter.
Work quickly when inverting the cake; letting it sit too long may cause the caramel to solidify and stick to the pan.
For smaller gatherings, halve the recipe and use a 9-inch round cake pan; adjust bake time to about 35 minutes.
Common mistake to avoid: Overmixing the batter can lead to a dense cake—mix just until combined!

Storing and Reheating Tips

To keep your Pineapple Upside Down Cake fresh, cover leftovers tightly with plastic wrap or store in an airtight container. It stays delicious at room temperature for up to 24 hours, or in the refrigerator for up to 4 days. For freezing, wrap individual slices in plastic and foil, then freeze for up to 2 months. Thaw in the refrigerator overnight before bringing to room temperature. To reheat, pop a slice in the microwave for about 15-20 seconds—just enough to melt the caramel topping and make the cake taste freshly baked!

FAQs

Can I use fresh pineapple instead of canned?
Absolutely! Just make sure to slice it thinly and remove any tough core before arranging in the pan. Fresh pineapple will work beautifully.

What if I don’t have almond extract?
No worries—swap in vanilla extract, or try coconut extract for a more tropical note. Either way, your cake will be flavorful.

Do I have to use maraschino cherries?
Not at all. You can skip them or replace with other candied fruit like blueberries or dried cranberries for a fun twist.

Can I make Pineapple Upside Down Cake in advance?
Yes! Bake it up to a day ahead, let it cool, and cover tightly. Give it a gentle reheat in the oven (covered with foil) at 300°F for 10 minutes before serving.

Why does my cake sometimes stick to the pan?
If the caramel sits too long before inverting, it can harden. Be sure to invert while the cake is still warm, and run a knife around the edge to help release it cleanly.

Conclusion

Best Pineapple Upside Down Cake is a delightfully retro dessert with timeless appeal. Its caramelized fruit topping, soft and buttery crumb, and easy preparation make it a winner for both weeknight treats and special occasions. Whether you’re a baking newbie or a seasoned pro, this cake promises amazing results with minimal fuss. Whip it up for your next family gathering or just because you’re craving something sweet and nostalgic. Don’t forget to check out my other easy cake recipes for even more baking inspiration. Happy flipping!