For the Boozy Blackberries:
3½ cups blackberries
2 tablespoons sugar
2 tablespoons water
2 ounces vodka
For the Ice Pop Purée:
3 cups fresh pineapple chunks (about ½ whole pineapple)
⅓ cup cilantro leaves
⅓ cup banana slices (about ½ banana)
⅓ cup whole-fat Greek yogurt
2¼ ounces vodka
1 tablespoon fresh lime juice (juice of about 1 lime)
Pinch kosher salt
1. Make the boozy blackberries: Prepare an ice bath. In a medium saucepan over high heat, bring the blackberries, sugar and water, covered, to a boil. Remove the lid and continue to cook at a medium boil, stirring occasionally and gently mashing half of the berries using a wooden spoon, until the berries are soft and the liquid has reduced to a syrup, 10 to 12 minutes. Stir in the vodka and immediately remove from the heat. Pour the blackberries into a bowl set over the ice bath and cool completely.
2. Make the ice pop purée. In a blender, purée all the ingredients on high until smooth, 2 minutes.
3. Assemble the ice pops: Spoon 2 tablespoons of purée into the bottom of each ice pop mold. Layer with 2 tablespoons of the blackberries. Repeat with 1 more layer of each. Insert a popsicle stick and freeze until solid, 4 to 5 hours.
4. To serve: One at a time, dip a frozen ice pop mold into a bowl of warm water for 10 to 15 seconds. Gently pull the ice pop to release from the mold and serve.