Golden Rum-Spiked Pineapple Upside-Down Cake

By AislePrompt Editorial · Published 2026-06-10 · Updated 2026-06-10

How this recipe was made — this recipe was drafted by AislePrompt's AI-assisted pipeline from technique templates and USDA-sourced nutrition data, and published by AislePrompt Editorial — see how AislePrompt recipes are drafted and published.

A moist and caramelized upside-down cake infused with golden rum, topped with bright pineapple rings and maraschino cherries. This Caribbean-inspired recipe, ready in about 60 minutes, layers unsalted butter, brown sugar, pineapple rings into a dessert worth slowing down for — great for weekend baking, holiday tables, or any time you want a sweet payoff at the end of a meal. Each serving lands at about 320 calories and feeds 8, so it slots into a weekend bake or a special-occasion dessert tray. Tap "Plan a meal with the AI" below to drop this recipe into your week and send the ingredients straight to Instacart. Nutrition values are approximate, calculated from USDA FoodData Central (fdc.nal.usda.gov) — verify against ingredient labels for any health-driven dietary plan.

Prep: 15 min Cook: 45 min Serves 8 Caribbean cuisine 320 cal/serving

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Ingredients

1/4 cup (56 g) unsalted butter
1/2 cup (100 g) brown sugar
6 pineapple rings
6 maraschino cherries
1 cup (120 g) all-purpose flour
1 tsp baking powder
1/4 tsp salt
3/4 cup (150 g) granulated sugar
2 large eggs
1 tsp vanilla extract
3 tbsp golden rum
1/2 cup (120 ml) whole milk

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Instructions

Step 1: Preheat oven to 350°F (175°C). In a 9-inch round cake pan, melt 1/4 cup unsalted butter over low heat. Stir in 1/2 cup brown sugar until fully combined and caramelized, about 2 minutes.
Step 2: Arrange 6 pineapple rings over the caramel in the pan, placing 1 maraschino cherry in the center of each ring.
Step 3: In a medium bowl, sift together 1 cup all-purpose flour, 1 tsp baking powder, and 1/4 tsp salt.
Step 4: In a separate large bowl, beat 3/4 cup granulated sugar and 2 large eggs with an electric mixer on medium speed until pale and fluffy, about 3 minutes.
Step 5: Add 1 tsp vanilla extract and 3 tbsp golden rum to the egg mixture, mixing until combined.
Step 6: Alternately add the dry ingredients and 1/2 cup whole milk to the wet ingredients, beginning and ending with the dry, mixing gently until just combined.
Step 7: Pour the batter evenly over the pineapple and cherries in the pan, smoothing the top.
Step 8: Bake for 40-45 minutes until a toothpick inserted in the center comes out clean and the cake edges pull slightly from the pan.
Step 9: Let the cake cool in the pan for 10 minutes, then invert onto a serving plate. Allow to cool before slicing and serving.