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Pineapple Upside Down Popsicle

Fresh pineapple may play a starring role in this recipe, but it’s the vanilla wafers that tie it all together.

Pineapple Upside Down Popsicle


  • 400 g (2 cups) pineapple, peeled, cubed
  • 1 Tablespoon raw cane sugar
  • 360 ml (1½ cup) vanilla yogurt
  • 20 g (¼ cup) vanilla wafers
  • 10 Maraschino cherries


  1. Place pineapple on a metal baking sheet and sprinkle with sugar.
  2. Use kitchen butane torch to caramelize sugar on pineapple. If you don’t have a torch, turn on the broiler and place the baking sheet in the oven. Broil until sugar has caramelized, about 3 minutes. Allow to cool.
  3. Place pineapple and 1¼ cups (300 ml) yogurt into the Vitamix container and secure lid.
  4. Select Variable 1.
  5. Turn machine on and slowly increase speed to Variable 10, then to High.
  6. Blend for 1 minute. Rinse and dry container.
  7. Place vanilla wafers into the Vitamix container and secure the lid.
  8. Select Variable 5.
  9. Pulse by quickly turning the machine on and off 3 times.
  10. Combine the remaining ¼ cup (60 ml) yogurt and vanilla crumbs in a separate bowl and mix.
  11. To assemble Popsicles: Place a cherry in the bottom of each Popsicle mold. Divide pineapple mixture evenly into the Popsicle mold. Top with vanilla wafer mixture.

Chef's Notes

If you do not have Popsicle molds, you can use small, disposable cups. Adding more sugars or alcohol to your Popsicles will inhibit the freezing process. When trying to recreate your favorite Popsicle, understanding how ingredients freeze is critical. Using full-fat dairy ingredients produces a creamier result, but you can also use nondairy milks and yogurt. Popsicles that are mostly fruit will have a very hard, icy texture. Don’t let extra smoothie go to waste! Smoothie Popsicles are a great way to use up leftover smoothies. No artificial colors or flavors included.

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