12 Delightful Pineapple Upside Down Cake Recipes

The first time I tasted pineapple upside-down cake was at my grandmother’s kitchen table, a sticky-sweet slice flipped dramatically from the pan, revealing glistening pineapple rings studded with maraschino cherries. The caramelized brown sugar topping was pure magic, and the tender cake beneath soaked up every bit of tropical flavor. Those childhood memories flood back every time I bake one—it’s comfort food that feels like a sunny vacation.

Lately, I’ve been experimenting in my own kitchen, twisting the classic recipe into fun variations like boozy rum-infused versions for date nights or gluten-free options for friends with dietary needs. In a world obsessed with quick desserts, pineapple upside-down cake stands out for its wow-factor presentation and nostalgic charm—it’s easy to make, endlessly adaptable, and always a crowd-pleaser.

Classic Pineapple Upside Down Cake

This timeless recipe features juicy pineapple rings caramelized in brown sugar and butter, topped with a buttery yellow cake batter. Ingredients (serves 8): 1/2 cup unsalted butter, 1 cup brown sugar, 1 can pineapple slices (drained), 8-10 maraschino cherries, 1 1/2 cups flour, 1 cup sugar, 2 eggs, 1/2 cup milk, 1 tsp vanilla, 2 tsp baking powder. Melt butter and brown sugar in a 9-inch cast-iron skillet, arrange pineapple and cherries, then mix batter and pour over. Bake at 350°F for 30-35 minutes until golden; invert onto a plate.
It’s beginner-friendly, naturally moist from the fruit juices, and delivers that perfect sweet-tangy balance for any gathering.

Vegan Pineapple Upside Down Cake

A plant-based twist using coconut oil and almond milk for the topping and batter. Ingredients (serves 8): 1/2 cup coconut oil, 1 cup brown sugar, 1 fresh pineapple (sliced), cherries, 1 1/2 cups flour, 1 cup sugar, 1/3 cup applesauce (egg sub), 1 cup almond milk, 1 tsp vanilla, 2 tsp baking powder. Layer melted oil, sugar, fruit in skillet; whisk batter and bake at 350°F for 35 minutes.
Dairy-free and egg-free, it’s lighter yet indulgent, ideal for vegans craving nostalgia without compromise.

Gluten-Free Pineapple Upside Down Bliss

Made with almond flour and rice flour for a tender crumb. Ingredients (serves 8): 1/2 cup butter, 1 cup brown sugar, pineapple slices, cherries, 1 1/2 cups gluten-free flour blend, 1 cup sugar, 3 eggs, 1/2 cup milk, 1 tsp vanilla, 1 tsp xanthan gum. Prepare topping, mix batter, bake at 350°F for 40 minutes.
Perfect for celiacs, it’s fluffy and guilt-free while mimicking the wheat-based original.

Coconut Pineapple Paradise Cake

Infused with shredded coconut for a tropical crunch. Ingredients (serves 8): 1/2 cup butter, 1 cup brown sugar, pineapple slices, cherries, 1 1/2 cups flour, 1 cup sugar, 2 eggs, 1/2 cup coconut milk, 1 cup shredded coconut, 2 tsp baking powder. Add coconut to batter; bake as usual at 350°F for 35 minutes.
Elevates the cake with nutty texture and island vibes, boosting antioxidants from coconut.

Rum-Soaked Tropical Upside Down Cake

A grown-up version with dark rum glaze. Ingredients (serves 8): 1/2 cup butter, 1 cup brown sugar, pineapple, cherries, 1 1/2 cups flour, 1 cup sugar, 2 eggs, 1/2 cup milk + 1/4 cup rum, vanilla, baking powder. Drizzle rum over baked, inverted cake.
Relaxing and flavorful, the rum enhances pineapple’s natural sweetness for sophisticated dessert lovers.

Mini Pineapple Upside Down Cupcakes

Bite-sized for parties, baked in muffin tins. Ingredients (makes 24): 1/4 cup butter, 1/2 cup brown sugar, mini pineapple pieces, cherries, 1 1/2 cups flour, 1 cup sugar, 2 eggs, 1/2 cup milk, vanilla. Portion into tins, bake at 350°F for 20 minutes.
Portion-controlled fun, great for sharing and less commitment than a full cake.

Mango-Pineapple Fusion Upside Down Cake

Swaps half the pineapple for ripe mango. Ingredients (serves 8): 1/2 cup butter, 1 cup brown sugar, pineapple + mango slices, cherries, standard batter. Arrange mixed fruit, bake 35 minutes at 350°F.
Doubles tropical tang with mango’s creaminess, packed with vitamins A and C.

Chocolate-Drizzled Pineapple Upside Down Cake

Topped with melted chocolate post-bake. Ingredients (serves 8): Classic base + 1 cup chocolate chips. Bake standard, drizzle chocolate after inverting.
Combines fruity brightness with chocolate decadence for an irresistible upgrade.

Banana-Pineapple Upside Down Dream

Layers bananas with pineapple for extra moisture. Ingredients (serves 8): 1/2 cup butter, brown sugar, pineapple + banana slices, cherries, batter with 1 mashed banana added. Bake 40 minutes.
Ultra-moist from bananas, naturally sweet and potassium-rich.

Spiced Chai Pineapple Upside Down Cake

Infused with chai spices like cinnamon and cardamom. Ingredients (serves 8): Classic + 1 tsp each cinnamon, ginger, cardamom in batter. Bake as usual.
Warm spices add cozy depth, perfect for fall twists on summer flavors.

Skillet Pineapple Upside Down Cake

One-pan wonder in cast iron for rustic appeal. Ingredients (serves 8): Same as classic, cooked entirely in a 10-inch skillet at 350°F for 35 minutes.
No extra dishes, enhances flavor absorption from the iron skillet.

Nutty Pecan Pineapple Upside Down Cake

Toasted pecans in the topping for crunch. Ingredients (serves 8): Classic + 1/2 cup chopped pecans sprinkled in brown sugar layer. Bake 35 minutes.
Adds healthy fats and texture, making it hearty and satisfying.

Whether you’re reliving childhood favorites or trying bold new twists, these 12 pineapple upside-down cake recipes are sure to flip your dessert game—grab some canned pineapple, preheat your oven, and bake up some joy today!