In a small saucepan, make a simple syrup by combining the water with the sugar. Whisk over medium heat until sugar is dissolved.
In a large blender, combine simple syrup with frozen cherries (or fresh). Blend until pureed.
For the pitcher of margaritas, combine cherry mixture with tequila, triple sec, and lime juice. Refrigerate or serve immediately, stir together.
To garnish the glass, dip rim of glass in extra simple syrup (or water) and then dip in turbinado sugar. Add ice and margaritas. Place a slice of lime on each glass, enjoy!
Notes
Blend the cherries until completely smooth. The puree shouldn't have any lumps in it.
You don't have to go to top shelf, but don't cheap out on the tequila either. The flavor will come through, so a solid mid-range tequila is a good bet.
Have fun with the garnishes! Dipping the rim of your glasses in the turbinado sugar adds a sweet and pretty presentation. Lime slices or wedges also look great in contrast with the red drinks. You could add fresh cherries or even maraschino or fancy cocktail cherries on a skewer for extra cherry love.