In a blender or food processor, puree fresh pineapple chunks until smooth. Pour the pineapple puree into a medium saucepan.

Stir in 1 cup of sugar into the pineapple puree. Heat the mixture over medium heat, stirring occasionally, until the sugar dissolves and the mixture thickens slightly, about 10-15 minutes. Remove from heat and let cool completely.

In a large mixing bowl, whisk together heavy cream, whole milk, vanilla extract, and a pinch of salt until well combined.

Stir the cooled pineapple mixture into the cream mixture until fully combined. Cover the bowl and refrigerate for at least 2 hours or until thoroughly chilled.

Pour the chilled mixture into an ice cream maker. Follow the manufacturer’s instructions, typically churning for 20-25 minutes, until the ice cream reaches a soft-serve consistency.

Transfer the churned ice cream into an airtight container. Freeze for at least 4 hours or until firm.

Scoop and serve the pineapple ice cream in bowls or cones. Optionally, garnish with fresh pineapple slices or coconut flakes for an extra tropical touch.