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!

I love 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!

How to make this Gluten Free Pineapple Upside Down Cake Recipe - Step by Step

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.

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

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.

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.

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.
• 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.

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

Gluten Free Carrot Coconut Bundt Cake

GF 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

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!

Boozy Pineapple Upside Down Cake - Gluten Free

Jen Pinkston

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

Print Recipe Pin Recipe

Prep Time 15 minutes mins

Cook Time 1 hour hr

Total Time 1 hour hr 15 minutes mins

Course Dessert

Cuisine American

Servings 8 servings

Calories 359 kcal

Ingredients

  

1x2x3x

• 4 eggs
• 1 c coconut sugar
• ⅔ c crushed pineapple
• ⅓ c pineapple juice
• 1 teaspoon vanilla
• ½ teaspoon apple cider vinegar
• ⅓ c dark rum
• 1 ¾ c gluten free all purpose flour blend
• ½ c arrowroot flour or potato starch
• 1 teaspoon baking soda
• 1 ½ teaspoon baking powder
• Pinch of salt
• 3 tablespoon coconut oil melted
• 3 tablespoon brown sugar
• 6 pineapple rings
• Real maraschino cherries cut in half

Instructions

 

• 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.
• Add pineapple slices and cherries in the center of the pineapple slices and between them.
• In a heavy duty mixer, combine sugar and eggs until mixed well.
• Add remaining ingredients and mix well for at least 2 minutes*.
• 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.
• 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.
• Watch for the liquid at the bottom to stop bubbling, then place your serving platter on top of the pan and carefully flip.
• Allow to cake to release from the pan, you should begin to see the fruit pull away so can remove it.
• 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.

Nutrition

Nutrition Facts

Boozy Pineapple Upside Down Cake - Gluten Free

Amount per Serving

Calories

359

% Daily Value*

Fat

 

8

g

12

%

Saturated Fat

 

5

g

31

%

Cholesterol

 

82

mg

27

%

Sodium

 

326

mg

14

%

Potassium

 

161

mg

5

%

Carbohydrates

 

64

g

21

%

Fiber

 

4

g

17

%

Sugar

 

32

g

36

%

Protein

 

6

g

12

%

Vitamin A

 

164

IU

3

%

Vitamin C

 

9

mg

11

%

Calcium

 

96

mg

10

%

Iron

 

2

mg

11

%

* Percent Daily Values are based on a 2000 calorie diet.

Keyword gluten free cake, gluten free pineapple cake, pineapple cake from scratch, upside down cake

Tried this recipe?Let us know how it was!

Photography by Katie Jameson