How to Make It
Process chopped pineapple in a blender until smooth, about 30 seconds. Pour through a fine mesh strainer into a small saucepan; discard solids. (You should have 1 1/2 to 2 cups strained puree; discard anything in excess of 2 cups.) Bring puree to a boil over medium-high. Boil, undisturbed, 1 minute; remove from heat. Let cool completely to room temperature, about 30 minutes.
Place whipping cream in a chilled large metal bowl. Beat with an electric mixer on high speed until stiff peaks form, 3 to 4 minutes. Spoon about 1/4 cup whipped cream into a separate bowl; stir in condensed milk, and fold mixture back into whipped cream in chilled bowl. Fold in cooled pineapple puree.
Spoon pineapple mixture into a chilled freezer-safe 8- x 4-inch loaf pan; cover with parchment paper, placing parchment directly on surface of mixture. Freeze until firm, about 6 hours. Serve with pineapple wedges.