• 1/2 cup butter
  • 1/2 cup brown sugar
  • 1 can of pineapple rings in pineapple juice (or a fresh pineapple cored and sliced into rings)
  • 1/4 cup dark rum (I used Captain's)
  • 1/2 cup heavy cream
  • For the cake:
  • 2 cups flour
  • 3/4 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 3/4 teaspoon salt
  • 3/4 cup unsalted butter, softened
  • 1 1/3 cups sugar
  • 3 eggs, separated
  • 1 1/2 teaspoons vanilla extract
  • 1/4 cup fresh pineapple juice (save juice from can)
  • 1/2 cup buttermilk (add 1 tbsp lemon juice to milk)
  • Fresh or jarred Morello cherries

I have always wanted to try pineapple upside down cake, but it’s just not something you find often growing up in Boston.  Maybe I’m just looking in the wrong places. Anyways, I decided I needed to try it out for myself and I stumbled on a 5-star rated recipe from Foodnetwork by Curtis Aikens that looked amazing. Normally, I add my own touches to recipes, but since this one had such great reviews and this was my first time making this cake, I followed it almost exactly. The only changes I did make were converting half the batter into 12 cupcakes and the other half into a smaller cake and adding Morello cherries. Most recipes call for maraschino cherries, but I find them way too sweet and unnatural tasting. The cake and cupcakes turned out really tasty. I will definitely be making this again, maybe with all fresh fruit next time if I’m feeling ambitious.


Separate egg whites from egg yolks and leave out at room temperature. Egg whites are easier to whip when they’re not cold.

Combine butter and brown sugar in a 12-inch cast iron skillet (I used a non-stick) and heat until bubbly. Add pineapple andcaramelize, turning once. Remove from skillet and set aside.

Pour rum and cream into a skillet and cook over low heat for about 5 minutes, until thickened, stirring constantly with a whisk. Remove from heat.

Grease a 10-inch round cake pan and line with parchment paper. I would highly recommend using the parchment paper because the pineapple can be very sticky. Arrange pineapple rings to cover bottom of pan. I added extra cherries to fill in the spaces. Pour cooled sauce over pineapple and set pan aside.

If making cupcakes, spray the cupcake pan with cooking spray for baking. Cut the pineapple rings into small wedges and arrange around the cherry in the center. Cover with about a tsp. of cream sauce.


Sift together flour, baking powder, soda and salt. Set aside.

In a large bowl cream butter and sugar until light and fluffy. Add egg yolks, one at a time, beating after each addition. Add vanilla. Combine pineapple juice and buttermilk. Alternately add sifted dry ingredients and juice/buttermilk mixture to creamed mixture (begin and end with dry ingredients.) Whip egg whites to soft peaks and fold into batter.

Bake at 350 degrees about 1 hour, or until a tester comes out clean. Invert onto a serving platter. The cupcakes should take between 15-20 minutes. Since I used my amazing cupcake maker, they took only about 10 minutes. If you decide to split the batter into two cakes, make sure you still make for about 40-50 minutes. I made the mistake of cooking mine 30, only to find out after I flipped it that it wasn’t near done. Luckily, I salvaged it by cooking it for an extra 20 minutes right side up!


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