10 Nostalgic Pineapple Upside Down Cake Recipes

Growing up in the 80s, the scent of caramelizing brown sugar and juicy pineapple slices baking in the oven was the ultimate signal that Grandma was in the kitchen. Every family gathering featured her iconic pineapple upside down cake—golden cake studded with cherries, flipped dramatically to reveal its glistening top. It wasn’t just dessert; it was a hug on a plate, evoking warmth and nostalgia that I’ve chased ever since.

Lately, I’ve been experimenting in my own kitchen, reviving that classic with modern twists to make it healthier, boozier, or even vegan for today’s palates. These 10 recipes honor the original while adding unique flavors that transport you back in time or spark new memories. Whether you’re baking for a crowd or a cozy night in, pineapple upside down cake remains timeless comfort food.

Classic Pineapple Upside Down Cake

This timeless recipe mirrors the one from my childhood, using simple pantry staples for a moist vanilla cake topped with caramelized pineapple rings and maraschino cherries. Ingredients: 1/4 cup butter, 1/2 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, 1 tsp baking powder.
Melt butter in a 9-inch cast-iron skillet, sprinkle with brown sugar, arrange pineapple and cherries. Mix batter and pour over; bake at 350°F for 35-40 minutes until golden, then invert onto a plate. Its nostalgic charm lies in the perfect sweet-tangy balance, offering a stress-free bake that’s beginner-friendly and feeds 8 generously.

Vegan Pineapple Upside Down Cake

A plant-based homage to the original, swapping eggs and dairy for flax eggs and coconut milk while keeping the iconic upside-down magic intact. Ingredients: 1/4 cup vegan butter, 1/2 cup brown sugar, 1 can pineapple slices, cherries, 1 1/2 cups flour, 1 cup sugar, 3 flax eggs (3 tbsp flax + 9 tbsp water), 1/2 cup coconut milk, 1 tsp vanilla, 1 tsp baking powder.
Prep the topping as usual, whisk batter until smooth, bake at 350°F for 40 minutes, and flip. Dairy-free benefits make it inclusive for all diets, with a lighter texture that’s just as moist and evokes retro vibes without compromise.

Gluten-Free Pineapple Upside Down Cake

Using almond and rice flour, this version delivers the same chewy caramel top without gluten, perfect for nostalgic bakes at modern tables. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, pineapple slices, cherries, 1 1/2 cups gluten-free flour blend, 1 cup sugar, 2 eggs, 1/2 cup milk (or almond), 1 tsp vanilla, 1 tsp baking powder, 1/2 tsp xanthan gum.
Layer topping in skillet, blend batter gently to avoid toughness, bake 35-40 minutes at 350°F, invert carefully. It’s gut-friendly, with a tender crumb that rivals wheat versions, promoting wellness without sacrificing that childhood wow factor.

Coconut Pineapple Upside Down Cake

Infused with shredded coconut for a tropical 70s twist, this cake amps up the nostalgia with flaky texture and island flair. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, pineapple slices, cherries, 1 1/2 cups flour, 1 cup sugar, 2 eggs, 1/2 cup coconut milk, 1 tsp vanilla, 1 tsp baking powder, 1/2 cup shredded coconut.
Arrange fruit and coconut in melted butter topping, stir coconut into batter, bake 40 minutes at 350°F. The added moisture and chew from coconut benefits drier cakes, creating a vacation-like escape in every bite.

Rum-Infused Pineapple Upside Down Cake

Channel 1950s cocktail parties with a splash of dark rum in the topping and batter for boozy depth. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 2 tbsp rum (topping), pineapple slices, cherries, 1 1/2 cups flour, 1 cup sugar, 2 eggs, 1/2 cup milk, 1 tsp vanilla, 1 tsp baking powder, 2 tbsp rum (batter).
Caramelize topping with rum, mix into batter, bake 35 minutes at 350°F. The rum enhances flavors and tenderizes, offering adult nostalgia with a sophisticated edge—ideal for dinner parties.

Banana-Pineapple Upside Down Cake

A fruity fusion blending ripe bananas with pineapple for extra moisture and 80s lunchbox appeal. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, pineapple slices, cherries, 2 mashed bananas, 1 1/4 cups flour, 3/4 cup sugar, 2 eggs, 1/2 cup milk, 1 tsp vanilla, 1 tsp baking powder.
Top with fruit, fold bananas into batter, bake 40-45 minutes at 350°F. Bananas add natural sweetness and potassium, making it healthier and ultra-moist for guilt-free indulgence.

Spiced Cinnamon Pineapple Upside Down Cake

Warm cinnamon and nutmeg evoke fall harvest nostalgia layered into the classic summer fruit cake. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, pineapple slices, cherries, 1 1/2 cups flour, 1 cup sugar, 2 eggs, 1/2 cup milk, 1 tsp vanilla, 1 tsp baking powder, 1 tsp cinnamon, 1/2 tsp nutmeg.
Sprinkle spices in topping and batter, bake 35 minutes at 350°F. Spices boost antioxidants and comfort, transforming the cake into a year-round cozy treat.

Pecan Pineapple Upside Down Cake

Crunchy pecans in the caramel topping nod to Southern grandma recipes from the 60s. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, 1/2 cup chopped pecans, pineapple slices, cherries, 1 1/2 cups flour, 1 cup sugar, 2 eggs, 1/2 cup milk, 1 tsp vanilla, 1 tsp baking powder.
Press pecans into topping, pour batter over, bake 40 minutes at 350°F. Nuts add protein and texture contrast, elevating it to a hearty, satisfying dessert.

Chocolate-Chip Pineapple Upside Down Cake

Sneaky chocolate chips melt into the batter for a playful 90s kid-friendly upgrade. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, pineapple slices, cherries, 1 1/2 cups flour, 3/4 cup sugar, 2 eggs, 1/2 cup milk, 1 tsp vanilla, 1 tsp baking powder, 1/2 cup chocolate chips.
Fold chips into batter after topping prep, bake 35-40 minutes at 350°F. Chips bring gooey joy and calcium, merging fruit nostalgia with chocolate heaven.

Tropical Mango Pineapple Upside Down Cake

Fresh mango alongside pineapple screams 70s luau parties with vibrant, juicy layers. Ingredients: 1/4 cup butter, 1/2 cup brown sugar, pineapple slices, mango chunks, cherries, 1 1/2 cups flour, 1 cup sugar, 2 eggs, 1/2 cup coconut milk, 1 tsp vanilla, 1 tsp baking powder.
Alternate fruits in topping, bake batter 40 minutes at 350°F. Mango adds vitamins A and C, intensifying tropical nostalgia for brighter, bolder flavors.

These nostalgic pineapple upside down cake recipes are easy to whip up and guaranteed to spark joy and memories. Grab your skillet, preheat that oven, and treat yourself or loved ones to a slice of retro heaven—your taste buds will thank you!