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25 Delicious Pineapple Upside Down Cake Recipes

By Elisha Baba


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Pineapples bring back wonderful memories of Hawaii and when I visited the Dole Plantation. I love anything with pineapples. Mysweet grandmother use to love the sweet, juicy taste of pineapples too. I must have gotten the love from her!

Some say the first “Pineapple Upside Down Cake” recipe did not generate any popularity until sometime after Mr. Dole started canning hisDolepineapples (around 1903).

They are easy to make and super sweet & delish! With just a few ingredients you can make your very own– butter, brown sugar, cake batter, pineapples, maybe some pecans. A few other ingredients or fruit can be added too but only if you want to.

Pineapple Upside Down Cakes combine the three things I love so much: pineapples, sweet cake, and yellow. Without further ado, I have rounded up some of my favorite Pineapple Upside Down Cake recipes from around the blogosphere that you will surely love too!

Delicious Pineapple Upside Down Cake Recipes You Should Try

You can’t go wrong with a classic Pineapple Upside Down Cake for dessert, but did you know that there are dozens of different variations on the traditional recipe available? Today I’ve compiled a fun selection of twenty-five different recipes, incorporating various ingredients and catering to a wide variety of dietary requirements. Keep reading to discover new ways to serve this crowd-pleasing dessert that you’ll enjoy baking throughout the upcoming spring and summer months!

1. Pineapple Upside Down Skillet Cake

Cookie Dough and Oven Mitt shows us how to make this delicious skillet recipe that uses a cast iron skillet to create your classic pineapple upside-down cake. You’ll enjoy a traditional recipe that creates a massive 10-inch dessert that’s ideal for family gatherings and parties. With only twenty minutes of prep time needed and then fifty minutes to cook, it’s a hassle-free dessert that will have everyone in your family asking you to make this treat again and again.

2. Mason Jar Pineapple Upside Down Cake

For a moist individual portion of cake, you won’t want to miss this recipe from Totally the Bomb, which uses mason jars to hold your cake. To get the traditional cake taste, you’ll want to add a teaspoon of brown sugar to the bottom of each jar on top of the cherry. So once you tip the little cakes out of the jar, you’ll enjoy the syrupy topping that this cake is so well known for.

3. Pineapple Upside Down Cheesecake

This recipe from Restless Chipotle combines two of my favorite desserts in one recipe; cheesecake and pineapple upside-down cake. The cheesecake is lightly flavored with pineapple and then is topped with rum syrup, pineapple, cherries, and pecans. For the finishing touch, you’ll use a plumber’s torch to brulee the topping of this unique dessert.

4. Blueberry Pineapple Upside Down Cake

This blueberry pineapple upside-down cake creates a seasonal twist on the classic dessert. You’ll simply replace your maraschino cherries with blueberries for a version of this cake that you might think tastes even better than the original. This recipe from Dinner at the Zoo creates a thick single layer cake that will be sure to be enjoyed by your whole family this summer.

5. Pineapple Upside Down Cupcakes

All Recipes shares this simple cupcake recipe that transforms your favorite cake into small individual portions. These are a great option for transporting to a birthday party or family gathering, and you can make as many as you need to share with everyone. Each cake will still have its own portion of pineapple and cherry to experience all of the flavors of the full-size dish.

6. Pineapple Upside Down Cheesecake – Copycat Cheesecake Factory Recipe

If you’ve ever tried this cheesecake at your local Cheesecake Factory, you’ll know how mouthwateringly delicious it is. This Silly Girl’s Kitchen shows us how easy this recipe is to recreate at home. You’ll enjoy two layers of pineapple upside-down cake, which are stuffed with pineapple cheesecake for a decadent dessert that would be great for a birthday or special occasion.

7. Pineapple Upside Down Mini Bites

Midlife Healthy Living shares these adorable mini desserts that are great for family meals and holiday celebrations. Mini portions are ideal for kids and teens, and every bite of these little cakes will still contain the classic flavors of a large pineapple upside-down cake. You’ll need minimal time to prepare these bite-sized cakes, and you can use a yellow cake mix as the base of these cakes to save even more time and effort.

8. Coconut Flour Pineapple Upside Down Cupcakes

For a dairy-free, gluten-free, and refined sugar-free recipe, check out this pineapple upside-down cake from Confessions of a Fit Foodie. It uses coconut flour and almond flour in the mixture to create a mini dessert that can satisfy a wide variety of dietary requirements. It’s the perfect dessert to finish off a summer barbecue!

9. Pineapple Upside Down Cake Smoothie

Have you ever thought about transforming your dessert into a smoothie? The Dirty Floor Diaries has taken our favorite cake ingredients and created this delicious smoothie that’s refreshing and satisfying on a hot summer’s day. Packed with healthy ingredients such as macadamia nuts, pineapple, and almond or coconut milk, it’s a delicious treat that the whole family will love without the guilt associated with eating cake!

10. Spicy Pineapple Upside Down Cakes

Try out this spicy recipe from Hezzi-D’s Books and Cooks if you are looking to mix things up a little bit from your usual pineapple upside-down cake recipe. All you need to get the spiciness added to this dish is to simply add some Tabasco sauce to the recipe! While it might sound like a strange combination, you’ll love the additional smoky heat once you taste this dessert.

11. Cinnamon Pineapple Upside Down Cupcakes

For a mini bite of dessert for those days where you feel too stuffed from your main course, try out this recipe from Spaceships and Laser Beams. These mini cakes use cinnamon and brown sugar to make the perfect addition to any family party. If you love the flavor of pineapple and can’t get enough of it, consider replacing the milk with pineapple juice for extra flavor.

12. Cherry Pineapple Upside-Down Cake Bites

Rural Mom offers these fun mini cake bites that are perfect for an after school treat for your kids. This is such a quick and easy recipe to follow, and it uses minimal ingredients. Kids would also love making these with you in the summer break, and you’ll use a box of yellow cake mix to keep things even simpler. The mixture of cherries and pineapples creates a flavorful addition to the top of these cakes, and they are sure to be enjoyed by anyone who tries them.

13. Ole Smoky Moonshine Pineapple Upside Down Cake

For an adult dessert for your next dinner party with friends, try out this recipe from Nicki’s Random Musingswhich incorporates Ole Smoky Moonshine into the dish. You’ll start by taking the pineapple out of its can and then soaking it in the pineapple moonshine for up to eight hours to absorb as much flavor as possible. It’s a great recipe to try during the holidays and will impress any of your friends or family who try it!

14. Mini Pineapple Upside Down Cake

These mini desserts from Giggles Galore will be a hit at your next birthday party. For best results, use dessert ring molds to help layer and bake these individual portions. However, if you don’t have them, you can just use simple cupcake tins. These desserts will look absolutely stunning on your dinner table, and as you will just use a box of cake mix to make them, they require minimal skill or effort in the kitchen.

15. Salted Caramel Pineapple Upside Down Cake

Red Cottage Chronicles adds one of my favorite sauces to this cake, giving it a luxurious finish. You’ll make a homemade caramel topping with rum, brown sugar, and butter, which goes perfectly with the neatly arranged pineapple rings. It’s an attractive cake that would make a great centerpiece for any party.

16. Gluten-Free Grilled Pineapple Upside Down Cake

Simply Gluten Free shares this easy-to-follow recipe that allows you to make this dessert suitable for anyone on a gluten-free diet. You’ll use gluten-free flour instead of your regular flour, and then opt for pineapple canned with juice instead of heavy syrup. This recipe also encourages you to use organic butter, eggs, and sugars, but you can just use whatever you have in your pantry. If you are catering to anyone on a dairy-free diet, simply use a non-dairy butter substitute instead of regular butter.

17. Cast Iron Skillet Pineapple Upside Down Cake

This is one of the best classic pineapple upside-down cake recipes, thanks to Duke Manor Farm. Your cast-iron skillet is ideal for cooking this dessert in and allows you to layer pineapple around the edges of the cake for an aesthetically pleasing dessert. Once it’s cooked, make sure you leave it for five minutes to set before turning it out to serve.

18. Easy Delicious Pineapple Upside-Down Cobbler

For a new twist on your favorite dessert, try out this cobbler from Far From Normal. Once everything is assembled, you’ll just need to put it in the oven for up to an hour, or until the top is golden brown and bubbling. You can either serve this dessert plain or with ice cream or whipped cream on the top.

19. Pineapple Upside Down Cinnamon Rolls

You won’t believe how well the flavors of pineapple upside-down cake combine with cinnamon rolls until you try out this dish from Shaken Together. You’ll enjoy a whole pan of cinnamon rolls topped with pineapple and a buttery caramel sauce. It’s the ideal special breakfast for a weekend treat or a family brunch.

20. 15-Minute Mini Pineapple Upside Down Cakes

If you have just fifteen minutes to spare, you don’t have to miss out on enjoying dessert, thanks to this quick and easy recipe from About a Mom. You’ll enjoy a mini bite-size dessert that uses buttermilk biscuits to make this dish super quick to prepare. It’s ideal for those nights where you fancy something sweet but have no energy left to create a whole dessert.

21. Old-Fashioned Pineapple Upside-Down Cake

All Recipes shares this old-fashioned pineapple upside-down cake recipe because sometimes the best option is following a traditional recipe. You’ll need just twenty-five minutes to prep this cake and then thirty minutes to cook, so you’ll have dessert ready to serve in under an hour. It makes a delicious 10-inch cake that can serve up to twelve hungry family members!

22. Dried Cranberry Pineapple Upside-Down Cupcakes

For a fun variation on the classic recipe, these cupcakes from PickleBums use dried cranberries instead of cherries. It won’t take long at all to mix all of the ingredients together, and then you’ll just need to cook them in the oven for fifteen to twenty minutes before they are ready to serve. It’s a great recipe for kids’ parties or summer barbecues and won’t add any extra stress or hassle to your day as they are so quick to prepare.

23. Pineapple Upside Down S’more Cookies

For a fun camping or summer activity, try out these s’more cookies from Kids Activities Blog. They use pineapple and banana to add a little bit of fresh fruit to what is otherwise a very sweet treat! Kids will absolutely love roasting their marshmallows and being part of the hands-on fun when preparing these cookies. After your pineapple and marshmallows turn golden brown, simply slide them off and onto your chocolate chip cookies to serve.

24. Pineapple, Cinnamon, and Allspice Cake

All Roads Lead to the Kitchen offers up an exotic recipe that combines cinnamon, cloves, and allspice for a unique twist on this classic dessert. The syrup is laced with these ingredients, so they blend into the cake fully while in the oven. While it may sound like a fancy recipe, it will take no longer than your usual recipe to prepare. After you let it cool, serve with whipped cream or vanilla ice cream for the best results.

25. Pineapple Cakes… Right Side Up

These fun little jars of cake from Happy Hour Projects flips the classic cake on its head and lets the pineapple rings show on the top of the cake. Try to use jars that are about the same size as the pineapple rings to ensure things don’t get too messy! You’ll also add brown sugar on the top as well, to create the same effect as the regular upside down recipe.

Which one of these recipes are you most excited to try out first? There are so many fun variations on the classic pineapple upside-down cake that you’ll have new options to try out all summer long this year. Whether you opt for a mini or full-size version of the dessert, it’s bound to go down a treat with all of your family and friends. This classic dish can always be served alone or with whipped cream or vanilla ice cream on the side for an indulgent treat.

Celebrate today by making a Pineapple Upside Down Cake for yourself!

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