Gluten Free Pineapple Upside Down Cake

This Gluten Free Pineapple Upside Down Cake is a little bit special! Not only is it gluten free, but it is also made with a generous helping of rum and real maraschino cherries. Made from scratch, this cake is easy to make and a pure joy to eat!

Gluten Free Pineapple Upside Down Cake on a wooden board

Is it just me or did spring fly by? Does that happen for you, too? Maybe it’s just Texas. Memorial Day is the marker for summer here, when it’s 90 degrees and the afternoons are too hot to do much of anything. I don’t mind the warm summer days, though. I love that it’s barbecue season, swimming pool time, and that there are lots of travel plans on the calendar. On those super hot days, I always wish I was poolside, sipping a daiquiri with nothing on my mind. Those vacation vibes with a dash of tropical flair is where this boozy cake recipe is meant to take you. Plus, it’s perfect for a Memorial Day barbecue or picnic!

Pineapple Upside Down Cake always reminds me of my grandmother’s pineapple upside down cake, which was so good and always felt like it christened summer. I decided to adapt it with just a slight twist, yes it’s gluten free but also it has rum in it. I’m not so sure she would approve of that part, sorry grandma!

Ingredients to make Gluten Free Pineapple Upside Down Cake Batter in a stand mixer Sugar being sprinkled into a glass baking dish

How to make this Gluten Free Pineapple Upside Down Cake Recipe

  1. Preheat oven to 350 and pour melted coconut oil into a glass 9” baking dish.
    Sprinkle brown sugar into the pan evenly over the coconut oil.
  2. Add pineapple slices and cherries in the center of the pineapple slices and between them.
  3. In a heavy duty mixer, combine sugar and eggs until mixed well.
  4. Add remaining ingredients and mix well for at least 2 minutes*.
  5. Pour the batter over the pineapple slices and bake for 55-65 minutes** Cover the cake with aluminum foil if the cake starts to get too brown.
  6. When you pull your cake out run a knife along the outside edges. If your cake has slightly poofed at all on top, you can cut it to make an even surface for when you flip.
  7. Watch for the liquid at the bottom to stop bubbling, then place your serving platter on top of the pan and carefully flip.
  8. Allow to cake to release from the pan, you should begin to see the fruit pull away so can remove it.
  9. Best served slightly warm. Top with a scoop  of vanilla bean ice cream if desired.

Pineapple rings being laid into the glass dish

What makes this the best pineapple upside down cake?

There’s quite a few different ideas of how to make the perfect upside down cake, but I would say general there’s a few key staples. Pineapple rings don the top making for a gorgeous centerpiece and there’s always a moist yellow cake involved. In this case, we for sure carry on those traditions but add a boozy element with a spicy dark rum and a richness with real maraschino cherries. I’m not talking about those bright red things you got in your shirley temples when were 8, I’m talking about the original maraschino used to make perfect Manhattans.

Real maraschino cherries

Real maraschino cherries are liqueur-preserved but when prohibition happened we started making these preservative filled imitation versions of maraschino cherries. Real ones have a red color that is so deep, it’s almost black and their syrup is thick like molasses. The taste is nutty like Amaretto and fruit-forward, without the sharp taste that imitation maraschinos have. They are limited in availability and often have a price that matches. But in my opinion they are worth every penny, in both a cocktail and in this cake.

Batter being spooned over the pineapple rings Gluten Free Pineapple Upside Down Cake being prepped

Gluten free pineapple upside down cake from scratch

It is so easy to make this cake from scratch! It shouldn’t take you any longer than 15 minutes to prep this cake and then just pop it in the oven for around an hour. Easy peasy! Because there is a lot of liquid in this cake your best bet is to cook until a toothpick comes out clean, then cook for 5-10 more minutes. This will ensure it is baked fully and you don’t end up with a mushy texture.

Can you make gluten free pineapple upside down cake ahead of time?

Unfortunately, this isn’t the best cake to make ahead of time as the pineapple has a tendency to fall into the cake.It will still taste delicious but it won’t look as pretty as if it were freshly made. Any leftovers can be stored covered in the fridge for about 3 days.

Gluten Free Pineapple Upside Down Cake after being baked in the glass dish Gluten Free Pineapple Upside Down Cake being cut

Top tips for making gluten free upside down pineapple cake

  • Do try and get your hands on real maraschino cherries, they really do make a huge difference!
  • Be sure to mix the batter well.
  • Use a dark rum for the best flavor.

Be sure to check out these other delicious gluten free dessert recipes!

Gluten Free Carrot Coconut Bundt Cake

Gluten Free Carrot Cake Donuts with Goat Cheese Glaze

Gluten Free Overnight Pumpkin Spice Cinnamon Rolls Recipe

Blueberry Lavender Hand Pies Recipe (Gluten Free and Paleo!)

Gluten Free Apple Cake by Gluten Free On A Shoestring

A slice of Gluten Free Pineapple Upside Down Cake on a black plate with a fork A piece of Gluten Free Pineapple Upside Down Cake served on a black plate

So when you show up to your summer pool party or a memorial day picnic with this in hand, you may want a few little umbrellas to stick in the top, ok I’m kidding. But this cake sure does bring the daiquiri vibes wherever it goes. Instead of umbrellas maybe try some vanilla bean ice cream to top off this perfect summer dessert.

If you have tried this recipe I’d love to hear from you!  Be sure to leave a star rating and let me know what you thought!

Print

Boozy Pineapple Upside Down Cake – Gluten Free

  • Author: Lauren Daniel
  • Prep Time: 15 minutes
  • Cook Time: 60 minutes
  • Total Time: 75 minutes
  • Yield: 8 servings 1x
  • Category: Dessert
  • Cuisine: American

Description

Vacation vibes with a dash of tropical is sort of where this boozy cake recipe is meant to take you. 


Scale

Ingredients

  • 4 eggs
  • 1 c coconut sugar
  • c crushed pineapple
  • c pineapple juice
  • 1 tsp vanilla
  • ½ tsp apple cider vinegar
  • c dark rum
  • 1 ¾ c gluten free all purpose flour blend
  • ½ c arrowroot flour or potato starch
  • 1 tsp baking soda
  • 1 ½ tsp baking powder
  • Pinch of salt

Instructions

  1. Preheat oven to 350 and pour melted coconut oil into a glass 9” baking dish.
    Sprinkle brown sugar into the pan evenly over the coconut oil.
  2. Add pineapple slices and cherries in the center of the pineapple slices and between them.
  3. In a heavy duty mixer, combine sugar and eggs until mixed well.
  4. Add remaining ingredients and mix well for at least 2 minutes*.
  5. Pour the batter over the pineapple slices and bake for 55-65 minutes** Cover the cake with aluminum foil if the cake starts to get too brown.
  6. When you pull your cake out run a knife along the outside edges. If your cake has slightly poofed at all on top, you can cut it to make an even surface for when you flip.
  7. Watch for the liquid at the bottom to stop bubbling, then place your serving platter on top of the pan and carefully flip.
  8. Allow to cake to release from the pan, you should begin to see the fruit pull away so can remove it.
  9. Best served slightly warm. Top with a scoop  of vanilla bean ice cream if desired.

Notes

*Well mixed batter is key in gluten free cakes.

**Because there is a lot of liquid in this cake your best bet is to cook until a toothpick comes out clean, then cook for 5-10 more minutes. This will ensure it is baked fully and you don’t end up with a mushy texture.

Keywords: gluten free pineapple cake, upside down cake, gluten free cake, pineapple cake from scratch

Photography by Katie Jameson

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  1. Jessica Camerata

    05/22/2019

    I have never had pineapple upside down cake, shocker! This look so good i may need to try it!

    xo Jessica
    My Style Vita

  2. This looks so good! As soon as I’m done with my candida diet, I am making this!

    Jennifer
    Effortlessly Sophisticated