Grilled Pineapple Upside Down Cake

The scent of caramelized sugar and warm pineapple instantly transports me back to my grandmother’s kitchen. She always had a pineapple upside-down cake gracing her countertop, its golden, glistening surface a beacon of love and deliciousness. While her version was baked to perfection in a cast iron skillet, I’ve found grilling the pineapple first adds a smoky sweetness that elevates this classic dessert to a whole new level. It’s a little kiss of summer sunshine in every bite, and I can’t wait to share this twist on a beloved family favorite with you.

Recipe Overview

• Prep Time: 20 minutes
• Cook Time: 30-35 minutes
• Total Time: 50-55 minutes
• Servings: 6
• Yield: 1 Cake
• Dietary Type: Not specified

Ingredients

• 1 fresh pineapple
• 2 tablespoons butter
• 1/3 cup dark brown sugar
• 1 teaspoon cinnamon
• 4-6 maraschino cherries
• 1 1/3 cups flour
• 2/3 cup granulated sugar
• 2 teaspoons baking powder
• 2/3 cup milk
• 1/4 cup butter, softened
• 1 egg
• 1 teaspoon bourbon vanilla

Equipment Needed

• 9-inch cake pan
• Mixing bowl
• Electric mixer or whisk
• Rubber spatula
• Grill or broiler
• Spraying sheet
• Toothpick

Instructions

1. Begin by prepping the pineapple. Peel it, then slice it into approximately 1/2-inch thick slices or rings. Remove the core from each slice. You can use a pineapple corer or a small paring knife for this.
2. Preheat your grill to medium heat. Alternatively, you can use your broiler. Place the pineapple rings on a sprayed sheet and grill or broil for about 5 minutes per side, or until they are lightly golden on the edges. The goal is to caramelize the sugars and impart a smoky flavor. Set the grilled pineapple aside. You might end up with extra pineapple, which is excellent for other dishes like teriyaki chicken. This step can be done a day or two in advance if you prefer.
3. Prepare the caramel base. Melt 2 tablespoons of butter in a 9-inch cake pan on the stove over low heat.
4. Stir in 1/3 cup of dark brown sugar, 1 teaspoon of cinnamon, and 1 tablespoon of water. Continue stirring until the butter is melted and the mixture is well combined. Remove the pan from the heat.
5. Arrange as many pineapple slices as possible flat on the bottom of the cake pan, nestling them close together in the caramel mixture.
6. Halve the maraschino cherries and place them in the empty cores and corners of the pineapple rings, adding a pop of color and sweetness. Set the prepared cake pan aside.
7. Prepare the cake batter. In a mixing bowl, combine 1 1/3 cups of flour, 2/3 cup of granulated sugar, and 2 teaspoons of baking powder.
8. Add 2/3 cup of milk, 1/4 cup of softened butter, 1 egg, and 1 teaspoon of bourbon vanilla.
9. Beat the ingredients together using an electric mixer or whisk until just combined, scraping down the sides of the bowl to ensure everything is incorporated. Be careful not to overmix the batter.
10. Spoon the batter evenly over the pineapple rings and cherries in the cake pan. Smooth the top of the batter carefully to cover the fruit completely.
11. Bake in a preheated 350-degree Fahrenheit oven for 30-35 minutes, or until a toothpick inserted into the center comes out clean.
12. Once baked, let the cake cool in the pan for 5 minutes. This allows the caramel to slightly set and prevents the cake from sticking when you invert it.
13. Loosen the sides of the cake from the pan using a knife or spatula. Invert the cake onto a serving platter. If any pineapple slices stick to the pan, gently remove them and place them back on the cake.
14. Serve the Grilled Pineapple Upside Down Cake warm. To warm a cooled cake, microwave it for 15-20 seconds.

Expert Tips & Tricks

• For an even deeper caramel flavor, use dark muscovado sugar instead of dark brown sugar. Its molasses notes really complement the pineapple.
• Don’t skip the grilling step! It really concentrates the flavor of the pineapple and adds a wonderful smoky char. If you don’t have a grill or broiler, you can caramelize the pineapple in a skillet with a little butter.
• To prevent the cake from sticking, make sure your cake pan is well-greased, even though the caramel layer helps with this. You can also line the bottom of the pan with parchment paper.
• If your cake starts to brown too quickly in the oven, tent it loosely with foil.

Serving & Storage Suggestions

Serve the Grilled Pineapple Upside Down Cake warm, either on its own or with a scoop of vanilla ice cream or a dollop of whipped cream. The warmth of the cake melts the ice cream perfectly, creating a delightful contrast of temperatures and textures.

Leftover cake can be stored at room temperature for up to 2 days or in the refrigerator for up to 5 days. To reheat, simply microwave a slice for 15-20 seconds. You can also freeze the cake for longer storage. Wrap it tightly in plastic wrap and then in foil, and it will keep for up to 2 months. Thaw in the refrigerator overnight before reheating.

Nutritional Information

Nutrient	Amount per Serving	% Daily Value
Calories	449.4 kcal	N/A
Calories from Fat	123 g	28%
Total Fat	13.8 g	21%
Saturated Fat	8.2 g	41%
Cholesterol	65.3 mg	21%
Sodium	253.4 mg	10%
Total Carbohydrate	78.7 g	26%
Dietary Fiber	3.2 g	12%
Sugars	50.4 g	201%
Protein	5.8 g	11%

Note: Nutritional information is an estimate and can vary based on specific ingredients and portion sizes.

Variations & Substitutions

• Gluten-Free: Substitute the all-purpose flour with a gluten-free blend for a gluten-free version.
• Dairy-Free: Replace the butter with a plant-based butter alternative and the milk with almond or oat milk.
• Spiced Cake: Add a pinch of nutmeg or cardamom to the cake batter for a warmer, spicier flavor.
• Different Fruit: Experiment with other fruits, such as peaches, apples, or pears, for a seasonal twist.

FAQs (Frequently Asked Questions)

Q: Can I use canned pineapple instead of fresh?
A: While fresh pineapple is recommended for the best flavor and texture, you can use canned pineapple rings in a pinch. Be sure to drain them well before grilling.

Q: What if my cake sticks to the pan when I invert it?
A: Run a thin knife or spatula around the edges of the cake to loosen it. You can also place the pan on the stove over low heat for a minute or two to help melt the caramel slightly.

Q: Can I make this cake ahead of time?
A: Yes, you can bake the cake a day in advance and store it at room temperature. Reheat it slightly before serving.

Q: Why is my cake batter so thick?
A: Make sure you measure the flour accurately. Overmixing can also lead to a denser batter.

Q: Can I add nuts to the cake?
A: Absolutely! Chopped pecans or walnuts would be a delicious addition to the caramel base.

Final Thoughts

This Grilled Pineapple Upside Down Cake is more than just a dessert; it’s a celebration of simple ingredients transformed into something extraordinary. The smoky grilled pineapple, the rich caramel, and the moist, tender cake create a symphony of flavors and textures that will delight your taste buds. I encourage you to try this recipe and share it with your loved ones. It’s sure to bring a little sunshine into their day, just like my grandmother’s cake always did for me. And don’t be afraid to experiment – maybe a splash of rum in the caramel sauce next time? The possibilities are endless!