Pour 1 cup of cream into a medium sauce pan. Add sugar. Heat over medium heat until the sugar is dissolved.
In a separate bowl, stir together milk, remaining cream and vanilla extract. Add in warm cream and sugar mixture. Cover with plastic wrap directly on the cream mixture. Pop in the fridge for several hours or overnight.
Churn according to your ice cream makers directions. In the last 5 minutes of churning add in pineapple and cherries. Move ice cream to a freezer safe container and freeze. Enjoy!