Pineapple upside-down cake is one of my favorite kinds of cake. I have fond memories of enjoying the box-mix version throughout childhood but decided to attempt one from scratch once I got to college and had my own kitchen. The cakes made back then tasted great and looked pretty good, too. I had never perfected my recipe until last weekend when I made this one. Then I made it even better by adding rum! The pineapple flavor in this cake is delicate and perfectly complemented by a generous hint of spiced dark rum. In addition to the rum flavor, the presentation of this tipsy pineapple upside-down rum cake is what sets it apart. There are a few different methods of layering the fruit in a bundt cake but this is the prettiest, in my opinion.

pineapple slices and maraschino cherries caramelizing in brown sugar and butter

A bundt cake takes a little longer to bake than, say, a sheet cake but the result is undeniably gorgeous. This is the showstopper you want to serve a dinner party or impress with at the bake sale…the adult bake sale, of course. As far as the boozy-infusion, there are just a couple of extra steps to make this magic: poke the baked cake with holes all over then return it to the pan and slowly pour on a rum butter glaze.

poking holes in pineapple upside down cake

pouring butter rum glaze over pineapple upside-down cake

The cake will soak up all of that boozy goodness and be even better tasting for it. Voila! Tipsy Pineapple Upside-Down Rum Cake. The glaze is comprised of melted butter, sugar, pineapple juice, and, of course, dark spiced rum. Don’t worry, the finished product is moist without being soggy

pineapple upside-down rum cake soaking in butter rum glaze

This is a grown and sexy cake, meaning the rum is NOT really cooked out of  it so it isn’t necessarily family friendly. But, if you know me, you know I’m usually cooking for adults! You might also know that I love supporting companies that are local, small, minority-owned, and/or woman-owned. Texas Pure-Milling makes high-quality traditional flours and baking mixes with local ingredients in support of Texas farmers and, after receiving a few of their products, I decided to try out the all-purpose flour in this recipe. It worked very well and I plan to try one of the baking mixes next to stay tuned for that.

If you follow me on Instagram, you know I was on a baking and drink-making spree this past Saturday! We are in the thick of cherry season and I am testing cherry recipes of all types. I have pounds and pounds of cherries to work with so I would love to hear from y’all about what you want me to make. Let me know in the comments below if you have ideas.

pineapple upside-down rum cake with maraschino cherries and sliced pineapple

If you like boozy cakes, check out my Naked Bourbon Carrot Cake and if you want more pineapple, here’s my Pineapple Pound Cake. Thanks for reading!

In partnership with Texas Pure Milling. As always, all opinions are my own.

4.92 from 12 votes
An out-of-this-world delicious Tipsy Pineapple Upside-Down Rum Cake by Dash of Jazz
Tipsy Pineapple Upside-Down Rum Cake
Prep Time
10 mins
Cook Time
50 mins
Resting Time
1 hr
Total Time
2 hrs
An indulgent cross between a pineapple upside-down cake and a classic rum cake beautifully presented in a bundt shape.
Course: Dessert
Cuisine: American, Caribbean
Keyword: dessert with rum, drunken pineapple cake, how to make a rum cake, pineapple rum cake, pineapple upside down cake, pineapple upside down cake with rum, pineapple upside down rum cake, rum cake recipe
Servings: 14 servings
  • 1/2 cup milk
  • 3/4 cup butter melted
  • 2 cups all-purpose flour
  • 1 tablespoon baking powder
  • 1/2 teaspoon sea salt
  • 1 cup brown sugar packed
  • 3 large eggs
  • 2 teaspoons vanilla extract
Rum Glaze
  • 1/4 cup pineapple juice
  • 1/3 cup butter melted
  • 1/2 cup spiced dark rum
  • 1/2 cup sugar
Cake Topping
  • 1 can sliced pineapples and juice cut slices into half circles
  • 10 ounce jar of maraschino cherries
  • 3/4 cup brown sugar
  • 1/2 cup butter
  1. Preheat oven to 350 degrees. Add butter from topping ingredients into bundt pan and place in oven to melt for a couple of minutes.
  2. Meanwhile, add flour, sea salt, and baking powder to a bowl and whisk to combine. In another bowl, combine 1/2 cup pineapple juice from the can of slices, milk, butter, brown sugar, vanilla, and egg and mix until uniform.

  3. Add wet mixture to dry and stir until batter is uniform and no dry pockets remain. Set aside.

  4. Carefully remove pan of melted butter from oven and mix in brown sugar to create the topping. Arrange pineapple slices and cherries in pan as shown. Carefully pour cake batter over top.

  5. Place in oven and bake for 45-50 minutes or until a toothpick inserted into multiple parts of the cake comes out clean. Remove cake from oven and let sit for about 10 minutes then invert onto a platter and poke small all over the top and sides with a skewer or toothpick.

  6. Combine rum syrup ingredients in a small bowl and mix vigorously until uniform. Place cake back in pan and poke more holes into bottom of cake. Slowly pour rum syrup into the holes and allow cake to soak for about an hour before flipping again and serving.

pineapple upside down rum cake with text overlay

overhead view of pineapple upside down rum cake with text overlay