If you love the tropical sweetness of pineapple combined with the nostalgic charm of whoopie pies, you are in for a treat with this Pineapple Whoopie Pies Recipe. These delightful sandwich-style cakes burst with bright pineapple flavor in every bite, wrapped in soft, cakey rounds and filled with a luscious cream cheese frosting that’s perfectly tangy and sweet. Bringing together simple ingredients with a splash of sunshine, this recipe effortlessly transforms a classic dessert into an irresistible tropical experience that’s sure to brighten any day.

Ingredients You’ll Need
Whipping up these Pineapple Whoopie Pies requires just a handful of straightforward ingredients, each chosen to create the perfect balance of flavor and texture. From the moist pineapple cake to the creamy frosting, every component plays a vital role in crafting these delicious treats.
- Pineapple cake mix: The base that delivers a tender, fruity cake with minimal effort.
- Oil (½ cup): Adds moisture to keep the cakes soft and rich.
- Pineapple juice (½ cup): Enhances the cake’s pineapple flavor naturally.
- Eggs (3 large): Provide structure and help the cake rise perfectly.
- Butter (4 oz, softened): Creates a creamy, smooth frosting base.
- Cream cheese (8 oz, softened): Brings tangy richness to the filling.
- Vanilla extract (1 teaspoon): Adds depth and warmth to the frosting.
- Powdered sugar (1 cup + extra): Sweetens the frosting and dusts the final pies for a pretty finish.
- Crushed pineapple (½ cup, well drained): Adds juicy bursts and texture inside the frosting.
How to Make Pineapple Whoopie Pies Recipe
Step 1: Prepare the Pineapple Cake Batter
Start by preheating your oven to 350°F (175°C). In a large mixing bowl, combine the pineapple cake mix, oil, pineapple juice, and eggs. Whisk until you get a smooth batter with no lumps. This mix will be the foundation of your whoopie pies, packed with tropical flavors and a nice airy texture.
Step 2: Bake the Cake Rounds
Line baking sheets with parchment paper or a silicone mat. Use a tablespoon or cookie scoop to drop even rounds of batter about 2 inches apart onto the prepared sheets. Bake in the oven for approximately 8 to 10 minutes, or until the edges are lightly golden and a toothpick inserted in the center comes out clean. Once baked, remove and allow them to cool completely on a wire rack. This step ensures you’ll have tender, fluffy cake rounds to sandwich your filling.
Step 3: Prepare the Cream Cheese Frosting
While the cakes cool, cream together the softened butter and cream cheese in a mixing bowl until it’s smooth and fluffy. Add the vanilla extract and powdered sugar gradually, beating on medium speed until you have a sweet, spreadable frosting. Finally, fold in the well-drained crushed pineapple to give your filling that extra burst of tropical juiciness and texture.
Step 4: Assemble Your Pineapple Whoopie Pies
Once the cake rounds are completely cool, spread a generous amount of the cream cheese frosting on the flat side of one round. Then sandwich it with another cake round, pressing gently so the filling spreads edge to edge. Repeat with the remaining rounds. For a charming finish, dust the tops with a little extra powdered sugar to add a touch of sweetness and visual appeal.
How to Serve Pineapple Whoopie Pies Recipe

Garnishes
To elevate these whoopie pies even further, try garnishing them with a sprinkle of toasted coconut flakes or a tiny wedge of fresh pineapple on top. This adds not only a lovely visual element but also a textural contrast that complements the soft cake and creamy filling beautifully.
Side Dishes
These whoopie pies pair wonderfully with a scoop of vanilla ice cream or a light fruit salad to keep things fresh and vibrant. Serving them alongside a chilled tropical drink like a pineapple smoothie or a sparkling citrus punch makes for a complete and refreshing dessert experience.
Creative Ways to Present
For a fun twist, try stacking smaller whoopie pies to create mini pineapple towers perfect for parties or gatherings. You can also drizzle a little pineapple glaze or honey over the finished pies for an added touch of shine and sweetness that guests will love.
Make Ahead and Storage
Storing Leftovers
If you have leftovers, no worries! Store your Pineapple Whoopie Pies in an airtight container in the refrigerator. They will stay fresh and delicious for up to 4 days, making them a convenient treat to enjoy later or share with friends and family.
Freezing
You can freeze these whoopie pies by wrapping each one individually in plastic wrap, then placing them in a freezer-safe container or bag. Freeze for up to 2 months. When ready to enjoy, thaw them overnight in the fridge for best texture and flavor.
Reheating
To enjoy your Pineapple Whoopie Pies warm, briefly microwave them for 10 to 15 seconds. This softens the cake and slightly melts the cream cheese filling, turning them into a gooey, irresistible delight perfect for any time of day.
FAQs
Can I use a different cake mix instead of pineapple?
While pineapple cake mix highlights the tropical flavor, yellow cake mix is a fine substitute if you prefer a milder base. Keep the pineapple juice and crushed pineapple for that signature tropical touch!
Do I have to drain the crushed pineapple?
Yes, draining the crushed pineapple well is important to ensure your frosting isn’t too runny and that the whoopie pies hold together perfectly.
Can I make these gluten-free?
To make a gluten-free version, use a gluten-free pineapple cake mix and double-check all your other ingredients to be safe. The delicious pineapple flavor will still shine through beautifully!
Is cream cheese frosting necessary?
The cream cheese frosting is key to the tangy-sweet contrast that makes this Pineapple Whoopie Pies Recipe so special. You could try a simple buttercream, but the cream cheese adds that extra depth you won’t want to miss.
How large should the cake rounds be?
A tablespoon or small cookie scoop works well to create rounds about 2 to 2.5 inches in diameter. This size is perfect for easy sandwiching and makes for a delightful bite-sized treat.
Final Thoughts
This Pineapple Whoopie Pies Recipe captures the joyful spirit of tropical flavors in a playful, satisfying dessert your friends and family will adore. It’s approachable enough for a weeknight baking session but special enough for parties and celebrations. So next time you want to share a bit of sunshine with your loved ones, give these pineapple-packed whoopie pies a try — you’ll love how simple ingredients come together to create something truly unforgettable.
