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Taste of Caribe Royale with Chef Cain

Pineapple Upside Down Cake: An All-American Favorite with an Asian Twist


If you love Pineapple Upside Down Cake, you’re not alone. This classic dessert is a perennial favorite for summertime cookouts, potlucks and celebrations. Who can resist the caramelized sticky topping, mingling with juicy fruit and tender yellow cake?

The Pineapple Upside Down Cake comes from a long tradition of skillet cakes. Sometimes simple and sometimes elaborate, these cakes could be baked over an open flame or on a stovetop. Baking a cake in a skillet with toppings that are revealed when the pan is inverted is nothing new – cake recipes like this date back to the Middle Ages!

Upside-down cakes were included in recipe books around the turn of the century, but they rarely included pineapples. In the 1920’s canned pineapple had just started to become widely available and it became a very trendy ingredient, making Pineapple Upside Down Cake something hostesses would serve for only their most glamorous guests. Two earliest printings of the Pineapple Upside Down Cake recipe were in a 1924 Seattle charity cookbook, Pineapple Glacé, and a 1925 women’s magazine in a full-page ad for Gold Medal flour. Pineapple Upside Down Cake continued to be all the rage into the midcentury and beyond.

This all-American dessert is delightfully adaptable and fun to make at home. Join our Executive Pastry Chef Joshua Cain and learn how to make his unique version with fresh pineapple and an Asian twist, which we serve as a banquet option here at Caribe Royale Orlando.

Pineapple Upside Down Cake (serves 10)                                                                 

5 cups              Butter
6 cups              Sugar
1 tbl                 Vanilla Extract
¾ cup               Baking Powder
½ tsp                Salt
7 cups              All Purpose Flour
6 cups              Milk
10                    Eggs
10                    Sliced Fresh Pineapple Rings
10                    Amarena Kirsch Cherries

Brown Sugar Smear (recipe below)
Lemongrass Glaze (recipe below)

Equipment Needed

  • Mixing Bowl
  • Stand Mixer with Paddle Attachment
  • Rubber spatula
  • Paring Knife
  • Scoop
  • Baking Molds or Cast-Iron Pan


  • Cream butter and sugar together till light and fluffy.
  • Mix eggs in stages and scrape bowl after each stage.
  • Let batter mix in between each stage.
  • Sift all dry ingredients and mix in mixer.
  • Turn speed down to speed #2 and add milk slowly.
  • Scrape bowl one more time and scoop into pan or small molds.
  • Prep molds (or pan) with Brown Sugar Smear
  • Layer one pineapple slice with a cherry in the center.
  • Bake at 350 degrees Fahrenheit for 20-24 minutes.
  • Allow to cool for 30 minutes.
  • Top with Lemongrass Glaze.

Brown Sugar Smear   

3 cups              Brown Sugar
1 cup               Butter
1 cup               Honey
1 cup               Light Corn Syrup
1 tsp                Vanilla
1 tsp                Cinnamon

Equipment Needed

  • Pot
  • Spatula


  • Bring all ingredients to a boil and then cool.

Lemongrass Glaze

1 cup               Water
1 cup               Granulated Sugar
1 cup               Powdered Sugar
4 pcs                Lemongrass, split

Equipment Needed

  • Pot
  • Spatula
  • Knife


  • Bring sugar and water to a boil and then add the split lemongrass and let steep for 15 minutes.
  • Pour through a strainer into the powdered sugar and mix until smooth.
  • The glaze should be nice and shiny with no lumps.
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