Caribbean Rum-Spiced Pineapple Upside-Down Cake

By AislePrompt Test Kitchen · Reviewed by AislePrompt Editorial · ·

Moist pineapple upside-down cake with a caramelized rum-spiced topping, capturing the vibrant flavors of the Caribbean. This caribbean-inspired desserts ready in about 60 minutes layers divided unsalted butter, packed brown sugar, rings, drained 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

Instructions

  1. Step 1: Preheat oven to 350°F. In a 9-inch round cake pan, melt 4 tbsp unsalted butter over low heat. Stir in 3/4 cup packed brown sugar and cook until bubbly and caramelized, about 2 minutes.
  2. Step 2: Arrange 6 pineapple rings evenly over the caramel mixture in the pan, then place 6 halved maraschino cherries in the centers of the rings and in spaces between.
  3. Step 3: In a medium bowl, whisk 1 1/2 cups all-purpose flour, 2 tsp baking powder, 1/2 tsp salt, 1 tsp ground cinnamon, and 1/4 tsp ground nutmeg.
  4. Step 4: In a large bowl, beat 1 cup granulated sugar with 2 large eggs until thick and pale, about 3 minutes. Add 1/2 cup whole milk, 1 tsp vanilla extract, 2 tbsp dark rum, and 2 tbsp melted unsalted butter; mix to combine.
  5. Step 5: Gradually add the dry ingredients to the wet ingredients, stirring just until smooth.
  6. Step 6: Pour the batter over the pineapple and cherries evenly.
  7. Step 7: Bake for 40-45 minutes or until a toothpick inserted into the center comes out clean.
  8. Step 8: Let the cake cool in the pan for 10 minutes, then carefully invert onto a serving plate to reveal the caramelized pineapple topping.

Equipment for this recipe

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Frequently asked questions

How long does Caribbean Rum-Spiced Pineapple Upside-Down Cake take to make?

Total time is about 60 minutes (15 min prep + 45 min cook). Most home bakers find this fits a weekend afternoon; chill or store as the recipe directs before serving.

How do I store leftover Caribbean Rum-Spiced Pineapple Upside-Down Cake?

Cool fully before storing. Most baked desserts keep at room temperature in an airtight container for 2–3 days, or in the fridge for up to 5 days. Cream- or custard-based desserts must go in the fridge within 2 hours; reheat gently or serve cold per the recipe.

Can I substitute ingredients in Caribbean Rum-Spiced Pineapple Upside-Down Cake?

Yes — most ingredients in this recipe have flexible swaps. For oil, use any neutral high-smoke-point oil (avocado, grapeseed, refined coconut). For aromatics, dried herbs at ⅓ the volume of fresh work in a pinch. The full ingredient list is shoppable on Instacart so you can see substitutes in real time.

How do I scale Caribbean Rum-Spiced Pineapple Upside-Down Cake for a different number of people?

The recipe is written for 8 servings. Multiply each ingredient by (your serving target / 8). Cook time stays roughly the same up to 2x; for 3-4x batches, switch from a skillet to a sheet pan or stockpot so the food isn't crowded — overcrowding steams instead of browns.

What goes well with Caribbean Rum-Spiced Pineapple Upside-Down Cake?

Caribbean desserts like this pair well with a simple grain (rice, couscous, or crusty bread), a quick salad with acid (lemon vinaigrette, pickled onions), and a pan sauce or yogurt-based dip. Tap "Plan a meal with the AI" to get specific side suggestions.

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