One of our favorite things is finding new twists on classic recipes. Case in point? Pineapple upside-down cake! We’ve turned it into fudge and pancakes, and we’ve shrunken it into mini cakes and made it bundt style. We’ve even mixed up a pineapple upside-down cake shot for the 21+ crowd. After all that innovation, though, we finally decided it was time to try it old-school classic cake style— so that’s what we’re doing today!

This recipe is for the ultimate in classic Pineapple Upside-Down Cakes, with all the tropical tastes and colors you could crave, especially in these winter months when we’re all dreaming of vacation. It’s as gorgeous to see as it is to taste, and we’re betting you’ll feel the same after you watch us whip it up. Intimidated by the “upside-down” part? Don’t be! Our video and step-by-step recipe will guide you through. Check it out!

Pineapple Upside-Down Cake

Makes 1 9-inch cake
Prep Time: 15 minutes
Total Time: 1 hour


  • ⅓ cup butter, melted
  • ½ cup brown sugar
  • 1 (20 oz) can sliced pineapple, drained and pineapple juice reserved
  • 13 maraschino cherries (optional)
  • 2 eggs
  • ⅔ cup sugar
  • ⅓ cup pineapple juice, from canned pineapple
  • 2 teaspoons vanilla, divided
  • 1 cup sifted flour
  • ½ teaspoon baking powder
  • ½ teaspoon salt
Serving a slice of pineapple upside-down cakeTipHero


    1. Preheat the oven to 350 degrees Fahrenheit (175 degrees Celsius).
    2. Pour the melted butter into a 9-inch cake pan, coating the bottom. Sprinkle the brown sugar and half of the vanilla extract evenly over the top. Add 1 pineapple slice to the center of the pan. Arrange 6 pineapple slices, evenly spaced, around the center pineapple slice. Cut the remaining 3 pineapple slices in half, and place the half slices vertically around the side of the cake pan, with the rounded sides facing down.
    3. Add the maraschino cherries, if using, to the centers of the pineapple slices and in between each slice, and set aside.
  1. Using a hand mixer, beat the eggs on medium speed for about 5 minutes, until thick and lightened in color.
  2. Continue mixing and gradually add in the sugar. Add the reserved pineapple juice and the remaining teaspoon of vanilla extract.
  3. Sift together the flour, baking powder and salt.
  4. Add the flour mixture to the egg mixture, and mix until just combined.
  5. Pour the cake batter into the cake pan over the pineapple slices. Use a spatula to spread the batter to the edges.
  6. Bake the cake for 35 to 45 minutes, or until a toothpick inserted in the center of the cake comes out clean.
  7. Use an offset spatula to run around the edge of the cake to help it release from the pan. Allow the cake to cool for 5 minutes before placing a plate or platter over the top of the pan and carefully inverting it to release the cake.
Baked pineapple upside-down cake on white plateTipHero

We just love how colorful and festive the final result is! Though you can, of course, leave out the maraschino cherries if you so choose, we think they add something special to this cake and really help the pineapple slices pop even more. After all, who could resist a dessert that’s delicious and pretty?!

So how does this version of pineapple upside-down cake compare to ones you’ve had before? Have you ever attempted making it before, or did the “upside-down” part intimidate you? Do you think you’ll give this recipe a try? Let us know if you make it and how it turns out!

Recipe adapted from Kitchen Gifts