Using a small blender, immersion blender, or food processor, blend the cherries and water until almost smooth (some chunks are okay). If needed, add another tablespoon of water. Set aside.
In a bowl, combine the yogurt, maple syrup, and vanilla.
Layer each popsicle mold starting with some yogurt then some cherry purée.Top each with the remaining yogurt, leaving about an inch of space from the top.
Stick a knife into each mold to gently combine the cherry purée and yogurt.
Freeze for five to six hours or until completely frozen. Enjoy!