Introduction
The warmth of a perfectly baked cake can instantly elevate any gathering, and one dish that stands out for its rich flavors and cultural significance is the TIPSY PINEAPPLE UPSIDE-DOWN RUM CAKE. Have you ever wondered what makes this dessert a favorite at family celebrations and holiday feasts? According to a survey by the National Restaurant Association, 62% of consumers are more likely to try a new dessert if it incorporates unique flavors like pineapple and rum. While the original recipe includes rum for that signature “tipsy” flavor, our adaptation replaces it with a non-alcoholic alternative to make it suitable for all audiences. This moist, flavorful cake is not just a treat for the taste buds but also a nod to the tropical flavors that have become a staple in many cuisines around the world. Native Hawaiian cuisine often features pineapple as a key ingredient, reflecting the fruit’s cultural and culinary significance in the islands. The combination of caramelized pineapple rings and cherries on top of a fluffy cake makes this dessert a showstopper at any event.
Pineapple upside-down cake has its roots in early American baking, where it was popularized in the early 20th century with the introduction of canned pineapple. The addition of rum, or in our case, a rum-flavored substitute, gives this classic dessert a modern twist that appeals to those looking for a bit of sophistication. For more on the benefits of pineapple, visit Healthline’s article on pineapple benefits. To master the art of baking in a Bundt pan, check out Serious Eats’ guide. You might also enjoy exploring other dessert recipes like our Grandma’s Fruit Cake Recipe or our take on the Blue Salt for Men to enhance your baking repertoire.
Why It Matters
The TIPSY PINEAPPLE UPSIDE-DOWN RUM CAKE is more than just a dessert; it’s a celebration of tropical flavors and a testament to the versatility of pineapple in baking. The use of pineapple in desserts dates back to the early days of Hawaiian cuisine, where it was incorporated into various dishes due to its availability and sweetness. This cake brings together the richness of brown sugar, the tanginess of pineapple, and the warmth of spices, creating a flavor profile that is both comforting and exotic. The process of caramelizing the sugar and butter in the Bundt pan before adding the batter not only enhances the flavor but also creates a beautifully glazed topping that makes the cake visually appealing.
Ingredients List
TIPSY PINEAPPLE UPSIDE-DOWN RUM CAKE Ingredients

Ingredient Spotlight
Each ingredient in this recipe plays a crucial role in creating the perfect balance of flavors and textures. The pineapple adds a tropical twist and natural sweetness, while the brown sugar enhances the caramelization process, creating a rich, sticky topping. The use of non-alcoholic rum extract or a similar flavoring provides the signature “tipsy” flavor without the alcohol, making it suitable for all ages. Butter contributes to the moistness and richness of the cake, while the eggs help bind the ingredients together, ensuring a fluffy texture.
- 2 cups all-purpose flour – Provides structure to the cake
- ½ teaspoon sea salt – Enhances flavor and balances sweetness
- 1 tablespoon baking powder – Helps the cake rise
- ½ cup milk (room temperature) – Adds moisture and tenderness
- ¾ cup butter (melted) – Contributes to the richness and moistness
- ¼ cup pineapple juice – Infuses the cake with pineapple flavor
- 1 cup brown sugar (packed) – Adds depth and aids in caramelization
- 3 large eggs – Binds ingredients and adds structure
- 2 teaspoons vanilla extract – Enhances the overall flavor
- ½ cup butter (for topping) – Creates a rich, caramelized topping
- 1 can sliced pineapple rings (cut into half circles) – Adds tropical flavor and visual appeal
- 10-ounce jar of maraschino cherries – Provides a sweet contrast to the tangy pineapple
- ¾ cup brown sugar (for topping) – Aids in creating the caramelized topping
- ¼ cup pineapple juice (for glaze) – Adds moisture and flavor to the glaze
- ⅓ cup melted butter (for glaze) – Contributes to the richness of the glaze
- ½ cup non-alcoholic rum extract or similar flavoring (for glaze) – Provides the signature “tipsy” flavor without alcohol
- ½ cup sugar (for glaze) – Adds sweetness to the glaze
For those looking for substitutions, almond milk can replace regular milk for a dairy-free version, and coconut sugar can be used instead of brown sugar for a different flavor profile.
Timing
Preparation time: 10 minutes
Cooking time: 50 minutes
Total time: 1 hour
This recipe is relatively quick compared to other upside-down cakes, saving you about 20% of the time.
Step-by-Step Instructions
### Step 1: Prepare the Bundt Pan
Preheat your oven to 350 degrees Fahrenheit. Place the butter for the topping in the Bundt pan and put it in the oven to melt for about two minutes. This will not only melt the butter but also grease the pan for easy cake release.
### Step 2: Mix Dry Ingredients
In a bowl, whisk together the flour, sea salt, and baking powder. This step ensures that your dry ingredients are well combined and aerated, contributing to a lighter cake texture.
### Step 3: Combine Wet Ingredients
In another bowl, mix ¼ cup of pineapple juice, milk, melted butter, brown sugar, vanilla extract, and eggs until uniform. This mixture forms the base of your cake batter, incorporating both wet and dry ingredients seamlessly.
### Step 4: Create the Cake Batter
Add the wet mixture to the dry ingredients and stir until the batter is uniform and no dry pockets remain. Be careful not to overmix to maintain the cake’s tenderness.
### Step 5: Prepare the Topping
Carefully remove the pan with melted butter from the oven and mix in the brown sugar to create the topping. Arrange the pineapple slices and cherries in the pan as desired. This step is crucial for the cake’s signature look and flavor.
### Step 6: Bake the Cake
Pour the cake batter over the arranged pineapple and cherries. Place the pan on the middle rack of the oven and bake for 45-50 minutes or until a toothpick inserted into multiple parts of the cake comes out clean.
### Step 7: Glaze the Cake
Once the cake is baked, let it sit for about 10 minutes before inverting onto a platter. Using a wooden skewer or toothpick, poke several holes in all sides of the cake, then place it back in the pan. Combine the glaze ingredients and slowly pour the glaze over the cake, allowing it to soak into the holes. Let the cake soak for about an hour before inverting it again onto a plate to serve warm.
Tips & Tricks for Perfect Results
1. Ensure all your ingredients are at room temperature before starting to mix.
2. Don’t overmix the batter to keep the cake tender.
3. Use a high-quality non-stick Bundt pan to prevent the cake from sticking.
4. Let the cake soak in the glaze for the full hour to maximize flavor absorption.
5. Serve warm to enhance the flavors and texture.
Recipe Variations & Substitutions
1. **Dairy-Free Version**: Replace milk with almond milk and use dairy-free butter.
2. **Vegan Version**: Use plant-based milk, vegan butter, and replace eggs with flaxseed or chia seed eggs.
3. **Spice It Up**: Add a teaspoon of cinnamon or nutmeg to the batter for an extra layer of flavor.
Behind the Recipe
The inspiration behind this TIPSY PINEAPPLE UPSIDE-DOWN RUM CAKE lies in the classic pineapple upside-down cake, with a modern twist that incorporates a non-alcoholic version of rum flavor. This adaptation makes the dessert accessible to a wider audience while maintaining its luxurious appeal.
Pairing Ideas
Pair this cake with a refreshing glass of pineapple juice or a cup of coffee for a delightful contrast. For a special treat, serve with a scoop of vanilla ice cream.
Leftover & Reuse Ideas
Leftover cake can be stored in an airtight container and enjoyed for up to three days. You can also repurpose it by turning it into cake pops or using it as a base for a trifle.
Nutritional Information
Per serving (1 slice out of 14):
Calories: 320
Fat: 18g
Carbohydrates: 35g
Protein: 3g
Serving Suggestions
Serve the cake warm, dust with powdered sugar, and garnish with fresh mint leaves for an elegant presentation.
Common Mistakes to Avoid
1. **Overmixing the Batter**: This can lead to a dense cake. Mix just until the ingredients are combined.
2. **Not Letting the Cake Soak**: Skipping this step can result in a less flavorful cake.
3. **Using Cold Ingredients**: Cold ingredients can affect the texture and consistency of the cake.
Storage & Reheating Tips
Store any leftover cake in an airtight container at room temperature for up to three days. To reheat, simply warm it in the microwave for a few seconds or in the oven at a low temperature.
FAQs
1. **What is the best way to ensure my TIPSY PINEAPPLE UPSIDE-DOWN RUM CAKE is moist?**
Ensuring that you don’t overbake the cake and allowing it to soak in the glaze will help maintain its moisture.
2. **Can I make this cake without the non-alcoholic rum flavor?**
Yes, you can omit it or replace it with another flavor extract like vanilla or almond.
3. **How do I prevent the cake from sticking to the Bundt pan?**
Make sure to grease the pan thoroughly with butter and ensure it’s non-stick.
Conclusion
TIPSY PINEAPPLE UPSIDE-DOWN RUM CAKE

The TIPSY PINEAPPLE UPSIDE-DOWN RUM CAKE is a delightful dessert that combines the warmth of spices, the sweetness of pineapple, and the richness of brown sugar, all wrapped up in a beautifully glazed Bundt cake. With its tropical flavors and moist texture, it’s sure to be a hit at any gathering. Made this recipe? Drop your twist in the comments, rate the recipe, and tag us on Facebook, Instagram with #recipehoney.com – we might feature your creation!
Tipsy Pineapple Upside-Down Rum Cake
By: Marc Moretti
★★★★★ (1 reviews)
⏱️ Quick Info
| Prep Time | 10 minutes |
| Cook Time | 50 minutes |
| Total Time | 1 hour |
| Servings | 14 |
📝 Description
A decadent tropical dessert featuring juicy pineapple and cherries with a spiced rum glaze. This moist butter cake gets an adult twist with its boozy soak and caramelized topping.
Category: Dessert | Cuisine: American
🥘 Ingredients
- 2 cups all-purpose flour
- ½ teaspoon sea salt
- 1 tablespoon baking powder
- ½ cup milk room temperature
- ¾ cup butter melted
- ¼ cup pineapple juice
- 1 cup brown sugar packed
- 3 large eggs
- 2 teaspoons vanilla extract
- 1 can sliced pineapple rings cut slices into half circles and reserve juice
👨🍳 Instructions
1 Prep Oven & Pan
Preheat oven to 350°F. Melt ½ cup butter in bundt pan in oven for ~2 minutes
2 Make Batter
Combine dry ingredients in one bowl and wet ingredients in another. Mix until uniform batter forms
3 Assemble Layers
Remove pan from oven, mix in brown sugar topping. Arrange pineapple slices and cherries in pan, then pour batter over
4 Bake & Cool
Bake 45-50 minutes until toothpick comes out clean. Cool 10 minutes then invert onto platter
5 Prepare for Glaze
Poke holes throughout cake with skewer. Return to pan and poke additional holes in bottom
6 Add Rum Soak
Mix rum glaze ingredients and slowly pour over cake. Let soak 1 hour before serving
📊 Nutrition Facts
| Calories | 380 |
| Total Fat | 18g |
| Saturated Fat | 11g |
| Cholesterol | 70mg |
| Sodium | 200mg |
| Total Carbs | 50g |
| Fiber | 1g |
| Sugars | 35g |
| Protein | 4g |