Pineapple Upside-Down Cake (with rum)

Pineapple upside-down cake with cherries on a plate.

This fresh pineapple cake is a modern take on the classic pineapple upside down cake from scratch. My recipe uses golden rum, fresh pineapple and of course, a few cherries. The alcohol in this pineapple rum cake is balanced and not overpowering, though you can taste the caramely notes of rum. One bite of this upside down pineapple rum cake and you’ll hopelessly succumb to its lure. With a dollop of whipped cream or scoop of vanilla it’s a sublime dessert, anytime.

Removing the outer skin of the fresh pineapple and cutting it into planks to top the cake.

Inspired by Toni Tipton-Martin

Is there anything better than a from-scratch pineapple upside down cake? I’m sure there is…maybe… however, I’m not able to focus on the next thing, until I share this outrageous pineapple rum cake with you. The recipe is adapted from one I found in Jubilee, Recipes from Two Centuries of African American Cooking by Toni Tipton-Martin, however, hers called for pecans and canned, crushed pineapple. I only had fresh pineapple and no nuts, so I took her recipe in a different direction to stellar results. I can only imagine how good the original version is… Next time…

Her tome is a brilliant compilation and thoughtful homage to African American cooking. In fact, on my first run through, I bookmarked several must try recipes. The first one I tried, Curried Meat Pies, reminded me so much of the Caribbean flavors I grew up with that I was instantly transported back. The pineapple upside down cake was next on my list.

Get a copy for yourself!

{Side note: I’ve been making classic Southern and island-inspired fare from this book and it’s one you’ll want for your own cookbook collection. Trust me. Click the affiliate link to get your own copy of Jubilee, Recipes from Two Centuries of African American Cooking. }

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making the caramel rum sauce topping for the upside down pineapple rum cake.

Mention pineapple upside down cake and that same universal image will pop into your head. Rings of canned pineapple and buttons of maraschino cherries nestled into a buttery yellow cake. It’s the way my grandmother (and everyone’s grandmother) made this traditional dessert. Because it’s such a familiar cake, it comes with certain expectations and you probably don’t want to veer too far from the original. The flavors in this version mirror the classic, with the exception of a caramel-y round note of dark rum, which is present in the pineapple topping AND the golden butter cake.

Upside down pineapple rum topping:

  • Fresh Pineapple
  • Brown Sugar
  • Butter
  • Dark Rum
  • Maraschino Cherries

Tips for brown sugar rum topping:

  1. Place a 9″ cake pan over medium high heat on the stove.
  2. Add the butter and brown sugar and stir together as the butter melts. (Use an oven mitt to protect your hand while you hold the side of the pan to keep it steady.)
  3. Bring the butter and sugar mixture to a boil, stirring constantly, until the sugar dissolves.
  4. Stir in the rum and remove from the heat.

The design of the upside down cake with fresh pineapple and rum is really up to you. The most important part is to make sure the pineapple slices are evenly sliced between 1/8″ to 1/4″ thick.

Design the topping for fresh pineapple upside down cake

  1. Cut your pineapple into planks and arrange them in the pan to completely cover the bottom of the cake pan.
  2. Slice maraschino cherries in half (I left the stems on for presentation) and insert them between any gaps between the pineapple planks. If you leave the stems on, you’ll want to tuck it under a pineapple plank so it’s visible when the cake is flipped.
  3. You could arrange the fruit like spokes in a wheel, or make fun pineapple cutouts with cookie cutters. The only limits are your own imagination. (I took a cue from the 80’s and went with a geometric style pattern).
assembling fresh pineapple cake batter from scratch.

Next comes the batter for the pineapple rum cake. Just make sure your butter is at room temperature before you begin.

Pineapple rum cake batter ingredients

  • Flour
  • Baking Powder
  • Salt
  • Sugar
  • Butter
  • Milk
  • Vanilla Extract
  • Dark Rum
  1. Mix together the flour, baking powder and salt and set aside.
  2. Cream the butter and sugar together with a hand mixer until it’s very pale yellow, light and fluffy.
  3. Add the egg, milk, vanilla and rum. Beat to combine. (It’ll look a bit curdled, but that’s ok.
  4. Add the flour to the butter mixture and use a rubber spatula to stir until just combined.
adding dry ingredients to the batter.


  1. When the batter is ready, drop by spoonfuls over the pineapple in the cake pan and gently smooth it over (it doesn’t have to be perfect).
  2. Bake in the center of the preheated oven until the top is golden and a cake tester inserted into the center of the cake comes out clean.
  3. Let the cake cool for 10 minutes and then invert it onto a cake stand.
Topping the fresh pineapple topping with cake batter and baking.

Fresh pineapple cake is a stunner

Most women get starry-eyed thinking about designer shoesI’m impressed with particularly appealing desserts. I think you’d agree, though, that this dazzling pineapple cake is pretty spectacular. The fresh candied pineapple topping is beautiful to admire and it’s so flipping GOOD. I love the way the Maraschino cherry halves break up the visual goldenrod canvas with pantone alacrity and the sticky sugar-rum glaze settles into puddles where the cherry’s pit used to be.

Tasting notes from pineapple rum cake

  • The rum isn’t dominant, but it is noticeable and plays well with the butter and brown sugar topping — kind of like a rum-caramel sauce that’s baked into the cake and cradles the fruit.
  • “Soft and sweet with a rum back note” is the way I’d describe the cake itself. It’s got a moist texture that holds together when you press the back of your fork into it (and I’ve found that’s a good way to grab every single crumb from the plate).
  • This is especially good with a dollop of fresh whipped cream or a scoop of vanilla or rum raisin.

My husband was wowed by this fresh pineapple cake. Not only from the unique look, but the tropical sugar rush it delivered. This lovely dessert didn’t last but a few days in our house and I’m betting it will go just as quickly in yours.

More pineapple desserts:

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4.43 from 19 votes

Pineapple Rum Upside Down Cake

A modern version of the classic pineapple upside down cake… with golden rum.
Author: Lisa Lotts
Course Dessert
Cuisine American
Keyword cake, maraschino cherries, pineapple, rum
Dietary Restrictions Vegetarian
Prep Time 20 minutes
Cook Time 30 minutes
Total Time 1 hour
Servings 8



  • ¼ fresh pineapple
  • 4 tablespoons butter
  • ½ cup brown sugar
  • 2 tablespoons dark rum
  • ¼ cup maraschino cherries sliced in half vertically


  • 1 cup all purpose flour
  • 1 teaspoon baking powder
  • ½ teaspoon salt
  • ¾ cup granulated sugar
  • 6 tablespoons unsalted butter at room temperature
  • 1 large egg
  • cup whole milk
  • 1 teaspoon vanilla extract
  • 2 tablespoons dark rum


  • Preheat the oven to 350°.


  • Cut away the top of the pineapple and trim the bottom so that it sits upright on a cutting board. Trim away the skin and discard. Cut the pineapple vertically along one side of the core, so you have a half-moon chunk of pineapple. Use the larger half for a fruit salad or some other recipe.
  • Slice the remaining pineapple into 1/4″ thick planks. Arrange the pineapple into the cake pan, cutting extra pieces according to the space left in the pan to fill, so you have an idea of how it fits into the pan. Transfer the planks to a separate plate and set aside.
  • Slice the maraschino cherries in half, vertically, leaving the stem on one half if possible. Set aside.


  • Place an 9″ cake pan directly over the heat on your stove and add the butter. Melt over medium high heat and add the brown sugar. (Use a oven mitt to hold the cake pan while you stir.) Add the rum and cook, stirring constantly until the brown sugar has melted and the mixture is bubbly and frothy. Remove from heat.
  • Arrange the pineapple planks on top of the brown sugar mixture in an even layer. Fill any voids with the cherry halves, cut side down (tucking the stems beneath the pineapple, so they’ll show when you flip out the dessert). Set aside.


  • In a small bowl, combine the flour, baking powder and salt. Whisk to blend and set aside.
  • In a large bowl add the butter and sugar. Use a hand mixer and beat on medium high for about 3 minutes or until the butter mixture is very light and creamy in texture, scraping down occasionally with a rubber spatula.
  • Add the egg, whole milk, vanilla extract and rum and beat into the butter mixture. Mixture will look slightly curdled.
  • Add the flour mixture and stir until smooth and combined. Pour the cake batter over the pineapple in the cake pan and gently smooth it out over the fruit. Bake for 30 minutes or until a cake tester comes out clean.
  • Let the cake rest in the pan for 10 minutes. Run a sharp knife around the edges to loosen it from the pan.
  • Place a cake platter over the cake pan and in one swift movement, invert the cake onto the platter.
  • Cake can be served warm with whipped cream or ice cream as desired. (really good with sweetened rum spiked whipped cream.)


Calories: 368kcal | Carbohydrates: 52g | Protein: 3g | Fat: 15g | Saturated Fat: 9g | Cholesterol: 62mg | Sodium: 215mg | Potassium: 138mg | Fiber: 1g | Sugar: 38g | Vitamin A: 504IU | Vitamin C: 14mg | Calcium: 62mg | Iron: 1mg

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  1. 5 stars
    Just made this scrumptious pineapple upside down cake. Perfection!!

  2. Cynthia Thurston says:

    HELP! No mention of egg in ingredients list. Is it one egg????? Geez, I hope so – here I go!

    1. Yikes! My bad. Yes, it’s one egg (I’ve fixed the recipe to reflect that). Thanks for the heads up!

  3. 5 stars
    Looks delicious! Can’t wait to try this with my family. I know they’d go crazy!

  4. 5 stars
    Pineapple upside down cake is one of my mother’s signature retro desserts! Can you keep a secret? Your delicious recipe is even better than Mom’s!!!

  5. I love upside down cakes so much — and this one looks exceptional! Thanks for sharing!

  6. Pam Greer says:

    5 stars
    You had me at rum! Seriously! What a great way to elevate the classic pineapple upside down cake!

  7. 5 stars
    This is so good and so delicious! My kids have been requesting me to make it again!