whole pineapple upside down cake with pineapple rings, pecans, brown sugar caramel and maraschino cherries

Bourbon Pineapple Upside Down Cake Recipe

We were out to dinner at a restaurant somewhere that no one in our family remembers, but it was the girls’ first taste of Pineapple Upside Down Cake. And it was a good one for sure. Everyone loved the buttery goodness of this cake, mixed with the sweet caramel of brown sugar and the sharp flavor of the pineapple. So recently when they asked for me to make it at home, I came up with this easy Bourbon Pineapple Upside Down Cake recipe. It’s based on things we already had at home, and it turned out soooooo good.

The surprise addition of bourbon gave the classic cake a little kick, and just a hint of boozy flavor the kids didn’t even notice. For the adults it was a nice way to slip in a quick “cocktail” that tasted like a buttery Old Fashioned! (Don’t worry, it’s only a splash of bourbon.)

Old Fashioned - classic alcoholic cocktail with bourbon whiskey, bitter, cane sugar and ice in retro glasses on vintage bar counter
Maybe this easy Pineapple Upside Down Cake recipe is inspired by our love for Old Fashioneds? (photo by 5FA)

Bourbon Pineapple Upside Down Cake Recipe

This is not your grandma’s recipe. I updated this easy Pineapple Upside Down Cake recipe for modern tastes. Now it has a throw-back, Mad Men vibe combined with a tad of everything-old-is-new-again charm. I think you’ll like it. Plus it’s so darn easy – you can make it in a cast-iron skillet and pop it right into the oven to bake.

whole pineapple upside down cake with pineapple rings, pecans, brown sugar caramel and maraschino cherries
Looks so awesome right out of the pan, all full of caramel goodness.


  • 1/2 cup butter
  • 1 cup packed brown sugar
  • 1 can (20 ounces) sliced pineapple
  • 3/4 cup chopped pecans
  • 3 large eggs, separated yolks from whites
  • 1 cup sugar
  • 1 tsp vanilla extract
  • 1 cup flour
  • 1 tsp baking powder
  • 1/4 tsp salt
  • 1/3 cup bourbon
  • Luxardo cocktail cherries (or maraschino cherries will work too)
ingredients to make easy pineapple upside down cake at home
The ingredients for this easy recipe are pretty easy to source in your pantry at home.


  • Preheat oven to 375°.
  • Melt butter in a 10-inch cast-iron skillet. Add brown sugar and mix well until sugar is melted – careful not to overcook or the mixture will caramelize and harden. (Believe me, I learned this the hard way.) Turn off heat.
Mixing the melted butter and brown sugar gives off this unbelievably delicious aroma.
  • Drain pineapple, reserving 1/3 cup juice. Place 8 pineapple rings in a single layer over sugar in the same skillet. Place cherries in center of pineapple slices. Add pecans evenly on top. Set aside.
  • In a large bowl, beat egg yolks with an electric mixer until creamy. Add sugar gradually, blending completely. Mix in bourbon, reserved pineapple juice and vanilla.
  • In another bowl, combine the flour, baking powder and salt. Add flour mixture to batter gradually, and mix well.
  • In a small bowl, beat egg whites on high speed until stiff peaks form. Fold the egg whites into batter. Pour into skillet and make sure all surfaces are covered well.
  • Bake for about 30-35 minutes, or until a toothpick inserted in the center comes out clean. Let stand for a few minutes before turning upside down onto serving plate.
  • Serve warm.
slices of pineapple upside down cake with pineapple rings and maraschino cherries
Ready to serve up, this cake is easy to make, easy to slice and easy to eat!

This easy Bourbon Pineapple Upside Down Cake tastes great with a dollop of whipped cream or a scoop of vanilla ice cream. However, our family just loves it the way it is.

See? An old lady dish all suped up and ready to roll.

And for another delicious cake recipe from days gone by, try our famous Pistachio Pudding Cake recipe!


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