Using a hand (or stand) mixer, whip the cream until stiff peaks form.
Add sweetened condensed milk and vanilla and continue mixing until well incorporated.
Using a spatula, gently fold in the chopped cherries and chocolate pieces. If you like, reserve a handful or so to sprinkle across the top.
Pour the ice cream into a 9x5-inch loaf pan and top with remaining chocolate and cherries. Cover and freeze for 5 to 6 hours until frozen through.
Once ready to serve, remove from freezer and let sit for 5 minutes allowing it to soften just enough to fill an ice cream scoop. Scoop into bowls or cones and serve immediately.