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The Ultimate Homemade Pineapple Upside-Down Sundae

A perfect scoop of the homemade vanilla ice cream with pineapple swirl.

An elaborate, deconstructed Pineapple Upside-Down Sundae. This recipe features a from-scratch, custard-style vanilla ice cream with a homemade pineapple-caramel mixture swirled throughout. The finished ice cream is served in bowls over a slice of pound cake and a ring of pineapple, then drizzled with a separate homemade caramel sauce and topped with whipped cream and a cherry for the full sundae experience.

Ingredients

Scale
  • For the Ice Cream:
  • 3 cups heavy cream
  • 1 cup whole milk
  • 3/4 cup sugar
  • 1 tablespoon pure vanilla extract
  • Kosher salt
  • 5 large egg yolks
  • For the Pineapple Swirl & Caramel Sauce:
  • 1/2 cup heavy cream
  • 4 tablespoons unsalted butter, cubed
  • 1/2 cup sugar
  • 1/4 cup light corn syrup
  • One 8-ounce can crushed pineapple in juice
  • For Assembly:
  • 8 slices pound cake (1/2 inch thick)
  • 8 slices canned pineapple
  • Whipped cream, for serving
  • 8 cherries with stems

Instructions

  1. Make the Ice Cream Custard Base:
  2. In a medium saucepan, whisk together 3 cups heavy cream, the milk, 3/4 cup sugar, vanilla, and 1/2 teaspoon salt. Bring to a simmer over medium heat.
  3. In a medium bowl, beat the egg yolks. Slowly whisk 1 cup of the hot cream mixture into the yolks to temper them.
  4. Pour the tempered egg mixture back into the saucepan. Cook over medium heat, stirring constantly with a wooden spoon, for 6 to 8 minutes until the mixture thickens and reaches 180°F on a thermometer.
  5. Strain the custard through a fine-mesh sieve into a large bowl. Stir often until it cools to room temperature, then press plastic wrap directly on the surface and chill until cold, about 3 hours.
  6. Make the Pineapple Swirl and Caramel Sauce:
  7. Combine 1/2 cup heavy cream, the butter, and 1/2 teaspoon salt in a measuring cup.
  8. In a saucepan, cook 1/2 cup sugar, the corn syrup, and 1 tablespoon of water over medium heat until the sugar dissolves. Increase heat to medium-high and boil, swirling the pan occasionally, until the caramel reaches a medium amber color, about 3 minutes.
  9. Remove from heat and carefully whisk in the cream-butter mixture until smooth. Pour about 3/4 cup of this caramel sauce into a measuring cup and set aside for topping.
  10. Stir the crushed pineapple and its juices into the remaining caramel in the saucepan. Cook over medium heat for about 12 minutes until reduced and thickened. Let cool for 10 minutes, then puree in a food processor. Chill until ready to use.
  11. Churn and Finish the Ice Cream:
  12. Pour the cold custard base into an ice cream maker and churn according to the manufacturer’s directions.
  13. Transfer half of the churned ice cream to an 8-inch square metal pan. Swirl in 1/2 cup of the chilled pineapple puree.
  14. Add the remaining ice cream and repeat with the remaining pineapple puree.
  15. Cover with plastic wrap and freeze until firm, 2 to 3 hours.
  16. Assemble the Sundaes:
  17. Warm the reserved caramel sauce in the microwave for 30 seconds.
  18. Place a slice of pound cake in the bottom of each of 8 bowls. Top with a slice of pineapple.
  19. Add a scoop of the pineapple swirl ice cream.
  20. Top with a dollop of whipped cream, drizzle with warm caramel sauce, and garnish with a cherry.

Notes

  • An ice cream maker and a food thermometer are required for this recipe.
  • For faster chilling, you can set the bowl of hot custard in a larger bowl of ice water and stir until cold.
  • Pressing plastic wrap directly onto the surface of the custard prevents a skin from forming.

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