10 Sweet Pineapple Upside Down Cake Recipes for Retro Vibes

Nothing beats the nostalgic allure of a pineapple upside-down cake fresh from the oven, that glorious moment when you flip the pan and reveal the glistening caramelized pineapple rings studded with cherries. I still remember my grandma’s kitchen in the 80s, filled with the sweet, buttery aroma as she whipped up her version for family potlucks—sticky fingers, laughter, and seconds (okay, thirds) all around. It was pure retro magic, evoking diners and Tupperware parties.

Lately, I’ve been on a kitchen experiment binge, channeling those vintage vibes with modern twists. After hosting a 70s-themed dinner party, I baked batch after batch, playing with flavors like rum, coconut, and even chocolate to keep the classic alive but exciting. In a world of air-fryer trends, these cakes remind us why simple, show-stopping desserts never go out of style—they’re easy, crowd-pleasing, and perfect for today’s retro revival.

Classic Pineapple Upside-Down Cake

Start with the timeless base: melt 1/4 cup butter with 3/4 cup brown sugar in a 9-inch cast-iron skillet for the topping. Arrange 7-8 pineapple rings (canned in juice, drained) and maraschino cherries in the centers. For the batter, cream 1/4 cup butter with 3/4 cup sugar, add 2 eggs, 1 tsp vanilla, 1 1/2 cups flour, 2 tsp baking powder, 1/2 tsp salt, and 1/2 cup pineapple juice—mix until smooth. Pour over fruit, bake at 350°F for 35-40 minutes, then invert.
This retro icon is beginner-friendly, delivers gooey caramel perfection, and serves 8 with just 10 minutes prep—ideal for evoking childhood nostalgia without fuss.

Coconut Pineapple Upside-Down Dream

Layer the skillet with 1/4 cup melted butter, 3/4 cup brown sugar, pineapple rings, cherries, and 1/2 cup toasted shredded coconut. Batter: 1 1/2 cups flour, 1 cup sugar, 1/2 cup coconut milk, 2 eggs, 1/4 cup butter, 2 tsp baking powder, 1 tsp coconut extract. Mix wet and dry separately, combine, pour, bake 350°F for 40 minutes, flip.
The coconut adds tropical flair to the retro vibe, boosting flavor without extra calories—moist, nutty, and gluten-full satisfaction for 8-10.

Rum-Infused Pineapple Upside-Down Bliss

Topping: 1/4 cup butter, 3/4 cup brown sugar, pineapple slices, cherries—drizzle 2 tbsp dark rum over fruit. Batter: standard yellow (1 1/2 cups flour, 3/4 cup sugar, 2 eggs, 1/2 cup milk, 1/4 cup butter, leaveners), plus 2 tbsp rum and 1 tsp vanilla. Bake 350°F 35 minutes, invert warm.
Rum elevates the caramel with boozy depth, perfect for adult retro parties—antioxidant pineapple perks plus indulgent warmth for 8.

Vegan Pineapple Upside-Down Delight

Veganize the topping: coconut oil (1/4 cup), brown sugar (3/4 cup), pineapple, cherries. Batter: 1 1/2 cups flour, 3/4 cup sugar, 1 cup coconut milk, 1/4 cup oil, 1 tbsp vinegar (for “eggs”), 2 tsp baking powder, 1 tsp vanilla. Stir, pour, bake 350°F 40 minutes.
Plant-based and dairy-free, it’s lighter yet decadent—great for inclusive gatherings, with pineapple’s vitamin C shining through.

Gluten-Free Pineapple Upside-Down Gem

Topping same as classic. Batter: 1 1/2 cups gluten-free 1:1 flour blend, 3/4 cup sugar, 2 eggs (or flax eggs), 1/2 cup milk (or almond), 1/4 cup butter (or vegan), 2 tsp baking powder, 1/2 tsp xanthan gum. Bake 350°F 35-40 minutes.
Allergy-friendly retro fun—tender crumb rivals wheat, packed with fruit fiber for guilt-free indulgence.

Banana-Pineapple Upside-Down Fusion

Topping: butter-sugar base, alternate pineapple rings with banana slices, cherries. Batter: add 1 mashed banana to classic recipe (1 1/2 cups flour, etc.), boost with 1/2 tsp cinnamon. Bake 350°F 38 minutes.
Potassium-rich bananas amp creaminess and sweetness naturally—healthier twist on nostalgia for 8.

Chocolate Pineapple Upside-Down Surprise

Topping: classic with extra brown sugar. Batter: 1 cup flour, 1/2 cup cocoa, 3/4 cup sugar, 2 eggs, 1/2 cup milk, 1/4 cup butter, 1 tsp baking soda—fold in 1/2 cup chocolate chips. Bake 350°F 40 minutes.
Decadent chocolate meets tangy pineapple for a retro-modern mashup—antioxidants galore, mood-boosting treat.

Spiced Cinnamon Pineapple Upside-Down Cake

Infuse topping with 1 tsp cinnamon in sugar-butter mix, pineapple-cherries. Batter: classic plus 1 tsp cinnamon and 1/2 tsp nutmeg. Bake 350°F 35 minutes.
Warm spices evoke old-school diners—comforting, digestion-friendly with pineapple enzymes.

Mango-Pineapple Upside-Down Tropical Twist

Topping: pineapple halves with fresh mango slices, cherries, extra lime zest. Batter: sub 1/4 cup mango puree in classic mix. Bake 350°F 37 minutes.
Exotic fruit duo bursts with vitamins A and C—refreshing retro upgrade for summer vibes.

Pecan Pineapple Upside-Down Vintage Crunch

Topping: butter-sugar, pineapple-cherries, scatter 1/2 cup chopped pecans. Batter: classic yellow. Bake 350°F 40 minutes.
Nuts add Southern crunch and healthy fats—elevates the 50s potluck staple to crunchy perfection.

These 10 pineapple upside-down cake recipes bring back those feel-good retro days with easy bakes and endless wow-factor flips—grab your skillet, channel your inner grandma, and treat yourself or a crowd today!