Caribbean Rum-Glazed Pineapple Upside-Down Cake

By AislePrompt Test Kitchen · Reviewed by AislePrompt Editorial · ·

A moist, buttery cake topped with caramelized pineapple rings and a rum-infused glaze for a sweet tropical dessert. This caribbean-inspired caribbean ready in about 65 minutes pairs divided unsalted butter, packed light brown sugar, rings, fresh or canned pineapple rings for a weeknight-friendly dinner that comes together with one pan and minimal cleanup. Each serving lands at about 350 calories and feeds 8, so it slots cleanly into a weekly meal plan and pairs well with a quick salad or grain on the side. Tap "Plan a meal with the AI" below to drop this recipe into your week and send the ingredients straight to Instacart.

★ 4.3 (9 ratings) Prep: 20 min Cook: 45 min Serves 8 Caribbean cuisine 350 cal/serving
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Ingredients

Instructions

  1. Step 1: Preheat the oven to 350°F. Melt 4 tbsp unsalted butter in a 9-inch round cake pan over low heat. Sprinkle 3/4 cup packed light brown sugar evenly over the melted butter, then arrange 8 pineapple rings on top. Place one maraschino cherry in the center of each pineapple ring.
  2. Step 2: In a medium bowl, whisk together 1 1/2 cups all-purpose flour, 1 cup granulated sugar, 1 1/2 tsp baking powder, and 1/4 tsp salt.
  3. Step 3: In a separate bowl, beat 2 large eggs, then add 1/2 cup whole milk, 1 tsp vanilla extract, 2 tbsp dark rum, and 2 tbsp melted unsalted butter. Mix well.
  4. Step 4: Pour the wet ingredients into the dry ingredients and gently fold until just combined, being careful not to over-mix.
  5. Step 5: Pour the batter evenly over the pineapple and brown sugar in the pan. Bake for 40-45 minutes until a toothpick inserted in the center comes out clean and the edges pull away slightly from the pan.
  6. Step 6: Remove the cake from the oven and let it cool for 10 minutes. Run a knife around the edges to loosen, then invert onto a serving plate so the pineapple topping is on top. Serve warm or at room temperature to enjoy a rich Caribbean-inspired dessert.

Frequently asked questions

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

Total time is about 65 minutes (20 min prep + 45 min cook). Most home cooks find this fits comfortably into a weeknight; double the batch on Sunday for two dinners.

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

Cool to room temperature within 2 hours, then store in an airtight container in the fridge for up to 4 days. Reheat covered in a 350°F oven for 10-12 minutes, or microwave at 70% power in 60-second bursts to keep divided unsalted butter from drying out.

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

Caribbean caribbean 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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