In a small saucepan, simmer the halved cherries with 2 tablespoons of water over low heat until softened (about 3-5 minutes). Gently mash to release juices.
Boil 1 cup of water and steep the Earl Grey tea for 3-5 minutes. Remove the tea bag or strain loose leaves.
Add warmed milk to the saucepan with cherries and heat gently, stirring occasionally. If desired, add a cinnamon stick for flavor.
Stir in the vanilla syrup to sweeten your mixture.
Pour brewed tea into a mug and strain the cherry-milk mixture over it, pressing on the cherries to extract juice.