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An out-of-this-world delicious Tipsy Pineapple Upside-Down Rum Cake by Dash of Jazz

Tipsy Pineapple Upside-Down Rum Cake

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 rum cake
Prep Time 10 minutes
Cook Time 50 minutes
Resting Time 1 hour
Total Time 2 hours
Servings 14 servings
Calories 316 kcal



  • 2 cups all-purpose flour
  • ½ teaspoon sea salt
  • 1 tablespoon baking powder
  • ½ cup milk room temperature
  • ¾ cup butter melted
  • 1 cup brown sugar packed
  • 3 large eggs
  • 2 teaspoons vanilla extract

Rum Glaze

  • ¼ cup pineapple juice
  • cup butter melted
  • ½ cup spiced dark rum
  • ½ cup sugar

Cake Topping

  • ½ cup butter
  • 1 can sliced pineapple rings cut slices into half circles and reserve juice
  • 10 ounce jar of maraschino cherries
  • ¾ cup brown sugar


  1. Preheat oven to 350 degrees. Add butter from topping ingredients into bundt pan and place in oven to melt for about two minutes.

  2. Meanwhile, add flour, sea salt, and baking powder to a bowl and whisk to combine. In another bowl, combine ½ 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 pan on middle rack of oven and bake for 45-50 minutes or until a toothpick inserted into multiple parts of the cake comes out clean.

  6. Remove cake from oven and let sit for about 10 minutes then invert onto a platter.

  7. Using a wooden skewer or toothpick, pole several holes in all sides of the cake. Place cake back in pan and poke more holes into bottom of cake.

  8. Combine rum syrup ingredients in a small bowl and mix vigorously until uniform. Then slowly pour rum syrup over top of cake, allowing it to flow into the poked holes.

  9. Allow cake to soak for about an hour then invert it again onto a plate and serve warm. Do not refrigerate cake during this step.

Recipe Notes

This cake is best served immediately after the rum has had time to soak in so I don't recommend making it ahead. If you do need to make it in advance, bake the cake, remove it from the pan after 10 minutes, and allow it to fully cool then cover it and place in the refrigerator. Before serving, allow it to come to room temperature then make the rum sauce and resume the recipe steps from there.

Nutrition Facts
Tipsy Pineapple Upside-Down Rum Cake
Amount Per Serving
Calories 316 Calories from Fat 18
% Daily Value*
Fat 2g3%
Saturated Fat 1g6%
Trans Fat 1g
Cholesterol 44mg15%
Sodium 231mg10%
Potassium 180mg5%
Carbohydrates 65g22%
Fiber 2g8%
Sugar 50g56%
Protein 5g10%
Vitamin A 146IU3%
Vitamin C 4mg5%
Calcium 141mg14%
Iron 2mg11%
* Percent Daily Values are based on a 2000 calorie diet.