Pineapple Upside Down Trifle & Banana Pudding Cake by Chef Tommi V. of Vincent Country
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Pineapple Upside Down Trifle & Banana Pudding Cake

May 10, 2019

Mother’s Day is a day earmarked to celebrate moms. As a mom, I am fully aware that my children have been nurtured and cared for by many women! Nurture is an innate quality that most women have naturally and are taught by the seasoned women before them. Mother’s Day celebrates every woman, whether she birthed the child or not, for nurturing and loving children to life.

I have shared many times that I love through my food. Anytime I develop a recipe, I am generally thinking of a specific person. These two desserts are inspired by my Nana Edie and Aunt Alverna. My nana made a huge bowl of banana pudding for family gatherings. You never forget something that was a family tradition highly anticipated by all! One day I distinctly remember a pineapple upside down cake on her kitchen counter. I assumed my Aunt Alverna made it, because I associated her with baking. She is an excellent baker. I shared with my nana I want to learn how to bake like Aunt Alverna. She looked at me and said, “Who do you think taught her.” Spoken like a big sister! They both have influenced my legacy-inspired cooking.

There are multiple recipes within these two desserts. I have broken it down into individual steps. Do not be overwhelmed. Execute one at a time. They are all simple and worth every bit of the effort. Each component can be made the day before, with the exception of the bananas. You want to cut them right before serving, so you are not presenting a dessert with brown bananas.


Pound Cake

  • 3 cups flour
  • 2 cups sugar
  • 2 tablespoons baking powder
  • 1 teaspoon salt
  • 8oz sour cream
  • 4 eggs
  • 3 sticks of unsalted butter
  • 1 ½ cup of juice from pineapple chunks, set fruit aside
  • 1 teaspoon vanilla extract

Bourbon Caramel Sauce

  • 1 cup brown sugar
  • 1 stick unsalted butter
  • 1/3 cup heavy cream
  • 1 tablespoon bourbon

Caramelized Pineapples

  • 2 cans pineapple chunks
  • 1 can pineapple rings (5 rings)
  • ¾ cup brown sugar
  • 4 tablespoons unsalted butter

Toasted Pecans

  • 1 cup pecans
  • ¼ teaspoon salt
  • 1 tablespoon unsalted butter

Whipped Cream

  • 1-quart heavy cream, cold
  • 2 teaspoons vanilla
  • ½ cup powdered sugar

Banana Pudding Pound Cake

  • 1 5.1oz box vanilla pudding, prepared according to directions
  • 2 teaspoons vanilla
  • 1 can sweetened condensed milk
  • 4 sliced bananas, cut into coins
  • Bourbon caramel sauce
  • Pineapple Pound Cake, sliced


  1. Pineapple Pound Cake

    Butter and dust with flour (2) 5 by 9 in. loaf pans. Preheat oven to 350°F

  2. With a stand mixer or hand mixer beat butter, sugar, and salt until mixture becomes a pale yellow. Add in one egg at a time until well incorporated. Add sour cream, pineapple juice, and vanilla. Mixture will look curdled. Sift flour and baking powder into the mixture. Mix on low until batter is smooth. Be sure to scrap sides of the bowl to insure all of the ingredients are mixed in.

  3. Spoon batter into loaf pans alternating to distribute equal amounts of batter. Bake for 55 to 60 minutes on the middle rack. Start checking at 50 minutes. Note: Oven temperatures vary. once you are able to insert a toothpick and it comes out clean, your cakes are done.

  4. Let cool for 15 min. before turning out of the pan.

  5. Bourbon Caramel Sauce

    Add butter and brown sugar into a skillet on medium high. Once the butter is melted, add heavy cream. Whisk together and add bourbon. Bring sauce to a light boil, right above simmering bubbles. Remove from heat. Set aside.  *Makes enough sauce for both desserts.

  6. Caramelized Pineapples

    Add butter and brown sugar to a large skillet on medium high. Drain pineapple chunks and rings. Add chunks on one side of the skillet and rings on the other. Let the fruit develop caramel coloring before turning fruit. Let the color develop on all side. Remove from heat and set aside.

  7. Toasted Pecans

    In a skillet add all of the ingredients, on medium high. Mix together so the pecans are coated with butter and salt. Toast for 3-5 minutes. Set aside.

  8. Whipped Cream

    Add heavy cream to a stand mixer or in a bowl using a hand mixer. Mix until cream forms fluffy medium peaks. Add in vanilla and sugar and mix on low just long enough to incorporate. Set in the refrigerator until you are ready to assemble your trifle.

  9. Assemble Deconstructed Pineapple Upside-down Cake Trifle

    You will need a trifle dish. Cut a loaf of pound cake into cubes.

  10. Add cream to the bottom of the dish, layer with cake, pineapple chunks, pecans, and sauce. Repeat. Add your pineapple rings to the top layer. Serve immediately.

  11. Dessert 2: Banana Pudding Pound Cake

    Make pudding according to box directions. Add vanilla and sweetened condensed milk.

  12. Cut pound cake loaf into slices and arrange on a platter. Pour the pudding over the cake slices. Top with bananas. Ladle or spoon bourbon caramel sauce over the top. Serve immediately.