In a large mixing bowl, combine the whole milk and instant vanilla pudding mix. Whisk vigorously for about 2 minutes until the mixture thickens and becomes smooth.

In a separate bowl, beat the heavy cream on medium speed until soft peaks form, about 3-4 minutes.

Gently fold the whipped cream into the pudding mixture using a rubber spatula.

Stir in the chopped maraschino cherries, crushed pineapple, and golden raisins to the combined mixture. Add rum extract if desired.

Transfer the mixture to a loaf pan, cover with plastic wrap, and freeze for at least 6 hours or overnight.

Once set, let it sit at room temperature for a few minutes before scooping and serve in bowls.