Hali’imaile’s Pineapple Upside Down Cake

10 Servings
Prep Time 10 minutes
Cook Time 35 minutes
Rest 15 minutes
Total Time 1 hour

Hali’imaile’s Pineapple Upside Down Cake is rich and moist with sweet, tangy pineapple caramel topping. It’s the ultimate summer treat.

This Cake Recipe is the perfect copycat for Hali’maile General Store’s incredible pineapple upside-down cake. For more tasty pineapple desserts, try my Pineapple Upside Down Cupcakes or Pineapple Coconut Bundt Cake.

Sabrina’s Hali’imaile’s Pineapple Upside Down Cake Recipe

The Hali’imaile General Store (also often seen referenced as Haliimaile General Store) is an incredible restaurant on the island of Maui. It’s definitely a favorite restaurant with my family. We can’t get enough of the delicious menu items. Along with the fantastic food on their dinner menu, the Maui restaurant also makes the most incredible Upside-Down Pineapple Cake ever.

The pineapple cake is a favorite menu item, and after trying it again, I just couldn’t get the taste out of my head. It’s perfectly moist and rich with the most fascinating fruit topping made with Maui pineapple and caramel sauce.

It’s too good to only have it on vacation. So, I’m bringing you this recipe to enjoy all the flavors of the original restaurant cake from your own kitchen. You can follow this recipe for an incredible cake that’ll have you feeling like you’re on the Hawaiian islands, even if it’s the middle of winter. It just might become your new favorite cake!

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  • Pineapple: For the pineapple topping, you can use canned pineapple rings. However, I definitely recommend fresh pineapple. The fresh slices of pineapple give Hali’imaile Pineapple Upside Down Cake the perfect fresh, tangy flavor.
  • Cake Ingredients: You can make this cake taste just as good as the acclaimed restaurant dessert with a few pantry staples. You only need simple ingredients for the buttery vanilla pound cake itself like cake flour, white sugar, baking powder, milk, eggs, vanilla, and unsalted butter. They all combine into a smooth, buttery, yellow cake batter.
  • Caramel Topping: To make the caramel mixture, you’ll need additional butter and brown sugar. Stir the sugar into the melted butter until it combines into a rich, caramelized sauce.
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Kitchen Tools & Equipment

  • Stand Mixer: Use your stand mixer with a paddle attachment to make easy work of this basic pound cake batter. If you don’t have one you can use a handheld electric mixer or simply a large mixing bowl and your trusty whisk. 
  • Sifter: You’ll use a sifter to combine the dry ingredients. This will ensure they are all mixed together well so you can combine with the wet ingredients without over-mixing the batter.
  • Pot and Spoon: A medium pot and spoon to stir will work to cook your caramel mixture. It needs to all get melted together to pour into the bottom of the pan, which will eventually become the top. It will cook more in the oven and then when you flip the cake out of the pan, the sauce will melt down into and over the sides of the cake for the most beautiful and tasty finish.
  • Round Cake Pan: Use a metal, round cake pan to bake your cake. It will transfer the heat evenly to the cake and ensure that gorgeous caramelized top when it’s finished.
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How to Make

Time needed: 1 hour.

  1. Prep Time

    Start by preheating the oven temperature to 400 degrees, and take the butter out to let it soften at room temperature or in the microwave. You can also slice the pineapple rings before starting the recipe.

  2. Sift

    Sift the dry ingredients together. Hali’imaile’s Pineapple Upside Down Cake flour being sifted

  3. Wet Ingredients

    In a separate bowl, combine the milk, egg yolks, and vanilla. Hali’imaile’s Pineapple Upside Down Cake batter wet ingredients

  4. Dry Ingredients

    Then add the softened butter to the dry ingredients. Mix the soft butter in, scraping the sides as you go. Hali’imaile’s Pineapple Upside Down Cake dry ingredients going into batter in mixing bowl

  5. Finish Batter

    Then slowly add the wet ingredients to the flour and butter mixture. Mix until the buttery cake mixture is smooth.Hali’imaile’s Pineapple Upside Down Cake batter in mixing bowl

  6. Sauce

    To begin the caramel sauce, melt butter until it starts to bubble. Hali’imaile’s Pineapple Upside Down Cake butter melted in the pan

  7. Caramel

    Then add sugar. Mix until the mixture is smooth with a light golden brown colorHali’imaile’s Pineapple Upside Down Cake sugar sauce simmering

  8. First Layer

    Pour the caramel mixture into an ungreased, round, metal cake pan. Then layer the slices of pineapple on top of the caramel.Hali’imaile’s Pineapple Upside Down Cake pineapples in pan

  9. Second Layer

    Pour the butter cake batter on top, leaving about 1 inch of room to allow the cake to rise. Then bake for 35 minutes.Hali’imaile’s Pineapple Upside Down Cake batter being poured over pineapples in pan

  10. Bake

    Rotate the pan and continue baking the cake for another 15 minutes. You can use a toothpick to check that the center is cooked before removing the Pineapple Cake from the oven.Hali’imaile’s Pineapple Upside Down Cake fresh out of the oven

  11. Flip Upside Down

    Let the baked cake rest for 15 minutes. Once you let the cake cool slightly, carefully invert it on a serving plate so that the caramelized pineapple slices are on top. Remove pan and serve the Hali’imaile Pineapple Upside Down Cake.Hali’imaile’s Pineapple Upside Down Cake turned over out of the oven

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Can this recipe be made ahead of time?

While this recipe is best made and served fresh, you could definitely prepare the sugar caramel topping and pineapples. Lay them out in the pan, then cover and refrigerate over night. Mix the cake batter and bake the cake as directed. If you’re really in a pinch, you can make Hali’imaeile Pineapple Upside Down Cake one day ahead of time. Much earlier than that and the cake will not look nearly as good or hold the same texture. Cover it tightly to store over night and when you’re ready to serve it, warm it up in the oven for a few minutes. 

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Nutritional Information

Nutrition Facts
Hali’imaile’s Pineapple Upside Down Cake
Amount Per Serving
Calories 795 Calories from Fat 378
% Daily Value*
Fat 42g65%
Saturated Fat 25g156%
Trans Fat 1g
Polyunsaturated Fat 2g
Monounsaturated Fat 12g
Cholesterol 258mg86%
Sodium 484mg21%
Potassium 265mg8%
Carbohydrates 101g34%
Fiber 2g8%
Sugar 79g88%
Protein 7g14%
Vitamin A 1454IU29%
Vitamin C 43mg52%
Calcium 244mg24%
Iron 1mg6%
* Percent Daily Values are based on a 2000 calorie diet.
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Baking Tips and Tricks

Master this gorgeous cake with these handy hints! 

  1. Achieving Fluffy Cakes
    • Always ensure your baking powder or baking soda is fresh. Test its effectiveness by dropping a bit into hot water. If it bubbles, it’s good to go!
  2. Avoid Over-mixing Batter
    • Over-mixing can lead to dense baked goods. Mix just until the ingredients are combined for the best cake texture.
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What to Pair with Upside Down Cake

Drinks: You can always serve this delicious cake, or any cake with a tall glass of cold milk. However, why not add some more flavors and make this dessert extra special? Try making your own fresh Strawberry Lemonade, or a vanilla, pineapple, or Strawberry Milkshake

Pre-Dessert Meal: If you are dying to make this cake and you want to build a meal around it, try out this tasty Hawaiian Garlic Shrimp, these juicy Hawaiian Pork Chops, or Slow Cooker Hawaiian Pineapple Chicken to keep with the awesome pineapple flavors from one course to the next.

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How to Store

  • Serve: You can leave this dreamy Hali’imaile Pineapple Upside-Down Cake at room temperature overnight. However, after that, it’s best to store the cake in the refrigerator.
  • Store: To store the cake in the fridge, cover it in plastic wrap and keep it for up to 3 days.
  • Freeze: If you want to keep the cake longer, you can freeze it for as long as 3 months.
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Ideas to Serve Pineapple Upside Down Cake

To make a nice presentation, I used a 3-inch round biscuit cutter to plate the slice and then did a swirl of fresh Whipped Cream topped with a bit of fresh pineapple.

Try serving up your slice of decadent cake with a scoop of Vanilla Ice Cream for the most refreshing island treat ever. You could also go tropical with your ice cream by serving it with Rainbow Sherbet, or fruity with a scoop of Strawberry Ice Cream, which pairs so nicely with pineapple flavors.

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Frequent Questions

Why’s it called “upside-down” cake?

It’s called upside-down cake because the pineapple and caramel topping is on the bottom when you bake the recipe. Then you flip the white cake upside down onto a platter so that the pineapples are on top before serving.

Can I freeze Pineapple Upside Down Cake?

You can freeze Maui’s Hami’ilmaile cake for later. Start by freezing the cake on a baking sheet for 1-2 hours. Once the outside has hardened, you can wrap it in plastic wrap followed by tin foil. Then freeze the cake for up to 3 months.

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Recipe Card

Hali’imaile’s Pineapple Upside Down Cake

Hali’imaile’s Pineapple Upside Down Cake is rich and moist with sweet, tangy pineapple, caramel topping. It's the ultimate summer treat!
Yield 10 Servings
Prep Time 10 minutes
Cook Time 35 minutes
Total Time 1 hour
Course Dessert
Cuisine Hawaiian
Author Sabrina Snyder


  • 2 cups cake flour
  • 1 1/4 cup sugar
  • 5 teaspoons baking powder
  • 1 teaspoon salt
  • 8 egg yolks
  • 1 1/2 cup whole milk
  • 1 teaspoon vanilla extract
  • 1 cup unsalted butter

Caramel Pineapple Topping:

  • 1 cup unsalted butter
  • 2 cups brown sugar
  • 1 pineapple , freshly cored and sliced, or 12 slices of canned pineapple rings


  • Soften butter to room temperature.
  • Preheat oven to 400 degrees

To prepare cake batter:

  • Sift all dry ingredients together.
  • Combine milk, egg yolks, and vanilla extract.
  • In a mixer, add softened butter to dry ingredients and mix slightly.
  • Scrape the sides of the bowl and continue to mix.
  • Gradually add the egg yolk mixture.
  • Mix until smooth.
  • To prepare the caramel:
  • Melt butter to boiling.
  • Add sugar.
  • Mix until smooth and mixture is a light brown color.
  • Pour the caramel mixture in an ungreased 12×3-inch round metal pan.
  • Layer the slices of pineapple on top of the caramel.
  • Next, pour the cake batter on top of the caramel and pineapple slices.
  • Leave about 1 inch of room at the top of the pan to allow the cake to rise.
  • Bake for 35 minutes.
  • Rotate and continue to bake for an additional 15 minutes or until center is cooked.
  • Let rest in the pan for 15 minutes.
  • Invert slowly on the plate you intend to serve in on.


Calories: 795kcal | Carbohydrates: 101g | Protein: 7g | Fat: 42g | Saturated Fat: 25g | Polyunsaturated Fat: 2g | Monounsaturated Fat: 12g | Trans Fat: 1g | Cholesterol: 258mg | Sodium: 484mg | Potassium: 265mg | Fiber: 2g | Sugar: 79g | Vitamin A: 1454IU | Vitamin C: 43mg | Calcium: 244mg | Iron: 1mg

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  • Cherries: Lots of people love adding cherries to their Pineapple Upside Down Cake toppings. Try adding maraschino cherries between the pineapple slices and at the center of the pineapple rings. You can also set some aside for garnish.
  • Coconut: Coconut is another addition you can try. Add toasted coconut flakes to the yellow cake batter or the caramel topping, depending on your preference.
  • Walnuts: You can also add some crunch to Hali’imaile Pineapple Upside Down Cake by mixing in walnuts with the caramelized topping.
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More Cake Recipes Featuring Fruit

Hali’imaile’s Pineapple Upside Down Cake collage of slice on plate with bite on a fork and whole round slice with whipped cream on side. Blue Banner with recipe name across center

About the Author: Sabrina Snyder

Sabrina is a professionally trained Private Chef of over 10 years with ServSafe Manager certification in food safety. She creates all the recipes here on Dinner, then Dessert, fueled in no small part by her love for bacon.

Sabrina Snyder is a professionally trained personal and private chef of over 10 years who is the creator and developer of all the recipes on Dinner, then Dessert.

She is also the author of the cookbook Dinner, then Dessert – Satisfying Meals Using Only 3, 5 or 7 Ingredients, published by Harper Collins.

She started Dinner, then Dessert as a business in her office as a lunch service for her coworkers who admired her lunches before going to culinary school and becoming a full time personal chef and private chef.

As a personal chef Sabrina would cook for families one day a week and cook their entire week of dinners. All grocery shopping, cooking and cleaning was done along with instructions on reheating. As a private chef she cooked for private parties and cooked in family homes in the evenings for families on a nightly basis after working as a personal chef during the day.

Sabrina has been certified as a ServSafe Manager since 2007 and was a longstanding member of the USPCA Personal Chef Association including being on the board of the Washington DC Chapter of Chefs in the US Personal Chef Association when they won Chapter of the year.

As a member of the community of food website creators Sabrina Snyder has spoken at many conferences regarding her experiences as a food writer including the Indulge Food Conference, Everything Food Conference, Haven Food Conference and IACP Annual Food Professionals Conference.

Sabrina lives with her family in sunny California.

Dinner, then Dessert, Inc. owns the copyright on all images and text and does not allow for its original recipes and pictures to be reproduced anywhere other than at this site unless authorization is given. If you enjoyed the recipe and would like to publish it on your own site, please re-write it in your own words, and link back to my site and recipe page. Read my disclosure and copyright policy. This post may contain affiliate links.


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