There’s something so cheerfully nostalgic about pineapple upside down cake, isn’t there? The glossy cherries, sweet golden fruit, that soft, buttery cake underneath—it’s like a time-traveling treat straight from grandma’s kitchen. But today, I’m giving this retro favorite a fun, portable twist with these Pineapple Upside Down Cake Jars. Think layers of juicy pineapple, tender vanilla cake, homemade whipped cream, and of course—those iconic maraschino cherries. All of this goodness is neatly tucked into individual mason jars for a dessert that’s party-ready, picnic-perfect, and honestly just a whole lot of fun to eat.
Pineapple Upside Down Cake Jars are sunshine layered in a jar. If you’re a fan of classic desserts reimagined with flair and convenience, then this recipe is going to become a staple in your rotation.
What Are Pineapple Upside Down Cake Jars?
Pineapple Upside Down Cake Jars are a modern, personal-sized version of the traditional pineapple upside down cake. Instead of baking the entire dessert in one large pan, we deconstruct the classic components and layer them beautifully into 8-ounce mason jars. Each jar offers a perfectly balanced taste of caramelized brown sugar, tart-sweet pineapple, moist vanilla cake, and a cloud of lightly sweetened whipped cream. Every spoonful captures the essence of the original but in a format that’s much easier to serve, store, and share.
These jars are perfect for outdoor gatherings, birthday parties, potlucks, bake sales, or anytime you want to serve dessert without slicing or plating.
Why You’ll Love This Recipe
There are a lot of reasons why Pineapple Upside Down Cake Jars deserve a spot on your dessert table:
- They’re portable and portion-controlled, making them perfect for parties or picnics.
- They offer the same beloved flavor of classic pineapple upside down cake but without the stress of flipping the cake out of a pan.
- You can use boxed cake mix or homemade batter depending on how much time you have.
- They store well in the refrigerator and taste even better the next day.
- Kids and adults both love them—seriously, these fly off the table at every event.
- They’re endlessly customizable. Want to add coconut or rum? Do it! Prefer strawberries instead of cherries? Go for it!
What Do They Taste Like?
The flavor is like a burst of tropical sunshine with a nostalgic hug. You get the tangy sweetness of pineapple, the soft and fluffy texture of vanilla cake, the richness of real whipped cream, and the cherry on top (literally) that ties everything together. The brown sugar adds a deep caramel note that infuses the pineapple, giving each layer a cozy, comforting sweetness.
It’s a dessert that feels celebratory yet familiar, indulgent yet approachable. Every spoonful is a perfect harmony of fruit, cake, and cream.
Benefits of Pineapple Upside Down Cake Jars
These jars are more than just pretty to look at. Here are a few practical reasons to love them:
- They eliminate the risk of flipping and breaking your upside down cake.
- You can prepare them in advance, which makes party planning a breeze.
- They’re easy to serve and require no cutting, plating, or utensils for guests.
- They keep well in the fridge for several days.
- Perfect for portion control if you’re trying to enjoy dessert in moderation.
Ingredients
To make about six 8-ounce jars, here’s what you’ll need:
For the Cake:
- 1 box vanilla or yellow cake mix (plus ingredients it calls for—usually eggs, oil, and water)
-or- - 1½ cups of your favorite homemade vanilla cake batter
For the Fruit Layer:
- 1 can (20 ounces) of pineapple chunks, thoroughly drained
- 1 jar maraschino cherries, drained and halved
- ¼ cup packed brown sugar
For the Whipped Topping:
- 1 cup heavy whipping cream
- 2 tablespoons powdered sugar
- 1 teaspoon vanilla extract
Optional Garnish:
- Extra maraschino cherries for decoration
- Toasted coconut flakes
- Crumbled cake crumbs or graham cracker crumbs for texture
Tools You’ll Need
- Six 8-ounce mason jars with lids
- Hand mixer or stand mixer for whipping cream
- Mixing bowls
- 9×13 baking pan
- Spatula and whisk
- Knife or kitchen scissors for chopping fruit and cake
Additions and Substitutions
This recipe is as versatile as it is tasty. Here are a few fun ways to change things up:
- Swap vanilla cake for pound cake if you want a denser, more indulgent base.
- Add a tablespoon of dark rum or rum extract to the whipped cream for a boozy twist.
- Use crushed pineapple for a softer, jammy texture.
- Substitute coconut whipped cream for a dairy-free version.
- Add toasted nuts or a sprinkle of cinnamon for extra complexity.
You can also swap the fruit to suit the season. Try peaches in summer or apples with cinnamon in fall.
How to Make Pineapple Upside Down Cake Jars
Step 1: Bake the Cake
Prepare the cake batter according to the instructions on the box or your chosen homemade recipe. Pour the batter into a greased 9×13-inch baking pan and bake as directed. Once done, allow the cake to cool completely. Once cooled, cut it into small, bite-sized cubes (about 1-inch pieces).
You can bake the cake the day before to save time. Just keep it covered at room temperature until ready to assemble.
Step 2: Prepare the Whipped Cream
In a chilled mixing bowl, beat the heavy cream with powdered sugar and vanilla extract until stiff peaks form. This should take about 3 to 5 minutes using a hand mixer on medium-high speed. Refrigerate the whipped cream until you’re ready to use it.
Step 3: Assemble the Jars
Now for the fun part—layering!
Start by spooning a bit of brown sugar into the bottom of each jar. Add a few pineapple chunks on top of the brown sugar. This mimics the caramelized fruit base of the original cake.
Next, layer in some cubed cake, followed by a few maraschino cherry halves. Repeat the layering with more cake and pineapple chunks. Finish with a generous dollop of whipped cream.
Top each jar with a whole cherry and, if desired, a sprinkle of toasted coconut or cake crumbs.
Step 4: Chill and Serve
Refrigerate the jars for at least 1 hour before serving. This helps the flavors meld and makes the dessert extra refreshing. These jars taste best within 2–3 days and should be kept chilled until ready to serve.
What to Serve With Pineapple Upside Down Cake Jars
These jars shine on their own, but if you’re building a whole menu or looking for drink pairings, here are a few ideas:
- Serve alongside this Moscato Sparkle Punch for a bubbly, fruity refreshment.
- For a tropical drink pairing, try this vibrant Strawberry Pineapple Mojito.
- Add a second mini dessert like these Strawberry Crunch Supreme Cups for a colorful dessert bar.
- Offer fresh fruit skewers or a platter of tropical fruits like mango, kiwi, and papaya.
- A scoop of vanilla or coconut ice cream on the side would be an indulgent bonus.
Tips for the Best Cake Jars
- Let your cake cool completely before cutting to avoid crumbling.
- Use a piping bag or spoon to cleanly layer whipped cream in the jars.
- Drain all fruit thoroughly to prevent soggy layers.
- Use clear jars so your beautiful layers are visible—it’s part of the charm!
- These jars are great for travel but keep them upright to preserve the layers.
Storage Instructions
Store the assembled jars in the refrigerator with lids or plastic wrap covering the tops. They’re best enjoyed within 48 to 72 hours. The cake will continue to absorb moisture from the fruit, so they actually improve a little over time.
You can also make the cake cubes in advance and freeze them for up to one month. Just thaw them before assembling the jars.
Do not freeze the fully assembled jars as the whipped cream may separate upon thawing.
Frequently Asked Questions (FAQ)
Can I use Cool Whip instead of homemade whipped cream?
Yes, especially if you’re in a hurry or need the whipped topping to be more stable for travel. It holds up well for make-ahead events.
Can I use fresh pineapple instead of canned?
Absolutely. Just make sure to chop it small and drain any excess juice to keep the layers clean and balanced.
Can these be made in larger jars?
Yes, you can use 12-ounce jars for a larger portion, or smaller 4-ounce jars for tasting-size servings. Just adjust the layering amounts accordingly.
Do I have to use maraschino cherries?
They’re traditional and provide that iconic look, but you can substitute with fresh cherries, dried cherries rehydrated in juice, or even strawberries for a twist.
Can I bake the cake directly in the jars?
Technically yes, but this recipe is designed for layering pre-baked cake. Baking in jars can be tricky and requires careful temperature control to avoid cracking.
In Conclusion: Why You’ll Want to Make These Again
Pineapple Upside Down Cake Jars are a delightful reimagining of a beloved dessert. They bring all the tropical flavor and cozy nostalgia of the original into a portable, fuss-free format that’s as fun to eat as it is to serve. Whether you’re hosting a backyard party, planning a romantic picnic, or just craving a spoonful of sunshine, these jars deliver in every way.
Their vibrant colors, bold flavor, and individual servings make them perfect for any occasion. And with so many ways to customize, you can return to this recipe again and again with fresh variations that keep things exciting.
More Recipes You’ll Love
If you loved this recipe, you might also enjoy:
- Moscato Sparkle Punch – a light, bubbly drink with fruit-forward flair.
- Strawberry Pineapple Mojito – perfect tropical refreshment with minty brightness.
- Strawberry Crunch Supreme Cups – a no-bake treat with texture, flavor, and color.
Nutritional Information (Per 8 oz Jar, Approximate)
- Calories: 320
- Total Fat: 15g
- Saturated Fat: 9g
- Carbohydrates: 40g
- Sugars: 28g
- Protein: 3g
- Fiber: 1g
- Sodium: 180mg
Pineapple Upside Down Cake Jars – A Tropical Dessert You Can Hold in Your Hand
Description
Pineapple Upside Down Cake Jars are a fun and portable twist on the classic! Layers of brown sugar-glazed pineapple, moist vanilla cake, fluffy whipped cream, and those signature cherries—all stacked into individual mason jars for a dessert that brings sunshine to any table. Great for parties, picnics, or make-ahead treats. These jars are as beautiful as they are delicious!
Ingredients
For the Cake:
1 box vanilla or yellow cake mix (plus eggs, oil, and water as required)
or1½ cups homemade vanilla cake batter
For the Fruit Layer:
1 can (20 oz) pineapple chunks, drained
1 jar maraschino cherries, drained and halved
¼ cup packed brown sugar
For the Whipped Cream:
1 cup heavy whipping cream
2 tablespoons powdered sugar
1 teaspoon vanilla extract
Optional Garnish:
Extra maraschino cherries
Toasted coconut flakes
Crumbled cake or graham cracker crumbs
Instructions
Bake the Cake:
Prepare cake mix according to box directions or use your favorite homemade vanilla cake recipe. Bake in a 9×13-inch pan. Once fully cooled, cut the cake into small cubes.Make the Whipped Cream:
In a chilled mixing bowl, beat heavy cream with powdered sugar and vanilla until stiff peaks form. Refrigerate until ready to use.Assemble the Jars:
In each 8 oz mason jar, start with a spoonful of brown sugar and a few pineapple chunks. Add a layer of cubed cake, then some cherry halves. Repeat with another layer of cake and pineapple. Finish with a generous dollop of whipped cream.Garnish and Chill:
Top with a cherry and optional coconut or crumbs. Chill for at least 1 hour. Best enjoyed within 2–3 days.
Notes
For a fun twist, add a splash of dark rum or rum extract to your whipped cream or cake batter.
Crushed pineapple works well in place of chunks for a softer texture.
Cake can be made a day ahead and stored at room temperature in an airtight container.
Use Cool Whip instead of whipped cream if you need extra stability for transporting or prepping ahead.
These jars are best served cold and will stay fresh in the fridge for up to 3 days.