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Place a loaf pan in the freezer to chill.
In a large mixing bowl or the bowl of a stand mixer, beat the cream cheese until smooth.
In a separate bowl, beat the heavy cream until stiff peaks form. Gently fold the whipped cream into the cream cheese until combined.
Add the sweetened condensed milk, 1 cup of pineapple tidbits, ⅓ cup of juice from the can, and vanilla extract. Fold gently until everything is fully incorporated.
Remove the chilled loaf pan from the freezer and pour the mixture into it.
If desired, top with extra pineapple tidbits.
Cover the loaf pan and freeze for 6–8 hours in a level spot, or until the ice cream is fully set.
Scoop into bowls or ice cream cones and serve.