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Easy Pineapple Whoopie Pies – Tropical Cream Filled Cookie Sandwiches Recipe

4.5 from 70 reviews

These Easy Pineapple Whoopie Pies are soft, cake-like sandwich cookies bursting with bright tropical pineapple flavor. Featuring tender pineapple-infused cookie layers and a smooth, creamy vanilla-cream cheese filling, they strike a perfect balance between fruity freshness and comforting sweetness. Ideal for spring and summer gatherings, these whoopie pies are easy to make with pantry staples, bring a cheerful vibe to any dessert table, and store well refrigerated or frozen.

Ingredients

Scale

For the Pineapple Whoopie Pies:

  • 2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter, softened
  • 1/2 cup light brown sugar, packed
  • 1/2 cup granulated sugar
  • 1 large egg
  • 1 teaspoon pure vanilla extract
  • 3/4 cup crushed pineapple, very well drained
  • 1/3 cup buttermilk

For the Cream Filling:

  • 1/2 cup unsalted butter, softened
  • 4 ounces cream cheese, softened
  • 2 1/2 cups powdered sugar
  • 1 teaspoon pure vanilla extract
  • 1 to 2 tablespoons heavy cream or milk, as needed for texture

Optional Garnish:

  • 2 tablespoons finely toasted coconut for sprinkling
  • 1 teaspoon finely grated lemon zest for a brighter finish

Instructions

  1. Prepare the oven and baking sheets: Preheat your oven to 350°F (175°C). Line 2 large baking sheets with parchment paper to prevent sticking and help with even baking.
  2. Mix the dry ingredients: In a medium bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt. Set aside to combine evenly.
  3. Cream the butter and sugars: In a large mixing bowl, beat the softened unsalted butter with light brown sugar and granulated sugar using a mixer on medium speed until light and fluffy, about 2 to 3 minutes. This aerates the mixture for soft cakes.
  4. Add the egg and flavoring: Beat in the large egg and pure vanilla extract until fully incorporated, ensuring the mixture is smooth and uniform.
  5. Add pineapple and buttermilk: Stir in the very well-drained crushed pineapple, then add the buttermilk. Mix on low speed just until combined. The batter will be soft but not overly runny.
  6. Combine wet and dry ingredients: Gradually add the dry flour mixture into the wet ingredients, mixing gently and just until there are no dry streaks left. Overmixing can toughen the cakes.
  7. Scoop the batter: Using a medium cookie scoop or about 1 1/2 tablespoons of batter, drop rounds evenly spaced about 2 inches apart onto the prepared baking sheets for even baking.
  8. Bake: Bake in the preheated oven for 10 to 12 minutes, or until the tops are set and springs back lightly to the touch. Avoid overbaking to maintain soft, cake-like texture.
  9. Cool completely: Let the cakes cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool fully, which is important to prevent the filling from melting during assembly.
  10. Make the filling: In a medium bowl, beat the softened butter and cream cheese together until smooth and creamy. Add powdered sugar and vanilla extract, and beat until fluffy. Add heavy cream or milk 1 tablespoon at a time to achieve a spreadable consistency.
  11. Assemble the whoopie pies: Pair the cooled cakes by size. Spread or pipe the cream filling onto the flat side of one cookie, then place the matching cookie on top, pressing gently to sandwich.
  12. Finish and chill if needed: Optionally, sprinkle the edges with toasted coconut or lemon zest for a finishing touch. Chill the assembled pies for 15 to 20 minutes to firm the filling before serving if preferred.

Notes

  • Drain the crushed pineapple very well to avoid overly loose batter and flat cakes.
  • Use a cookie scoop for consistent, even-sized cake layers.
  • Do not overmix the batter once dry ingredients are added to keep cakes tender.
  • Make sure butter and cream cheese for filling are softened for a smooth texture.
  • Store the whoopie pies in an airtight container in the refrigerator for up to 4 days; bring to room temperature before serving.
  • Whoopie pies can be frozen individually wrapped for up to 2 months; thaw overnight in the fridge.
  • Optional filling variations include vanilla buttercream, whipped frosting, or coconut frosting for tropical flair.
  • Add citrus zest or a pinch of cinnamon to the batter for flavor variations.

Keywords: pineapple whoopie pies, tropical dessert, cream filled cookies, pineapple cookies, whoopie pies recipe, soft cake cookies, summer dessert, party treats