Stir the fruit and 2 tablespoons honey together in a small saucepan over medium high heat. Bring to steady simmer, then let the mixture cook 8 to 10 minutes, until the fruit has a thick, jam-like consistency. Stir the fruit often to prevent burning. Remove the pan from the heat, then add the vanilla. Let the fruit cool to room temperature.
In a small bowl, stir together the yogurt, milk and 1 tablespoon of honey. Taste the mixture and add additional honey if you desire more sweetness. Transfer ¼ cup of yogurt to a small bowl, then add the granola and stir to coat. Coating the granola will help it to soften and freeze properly with the popsicles.
Lay out a popsicle mold on your work surface. Using a small spoon, add a large dollop of yogurt to the bottom of each. Next, add a small amount of the coated granola, then a spoonful of the cooked and cooled fruit. Gently tap the mold on the counter between each layer so that you remove any air pockets. Continue to layer the ingredients until the popsicle molds are filled. Tap the molds on the counter once more. Insert popsicle sticks, then freeze until the pops are solid, 6 hours or overnight.
To unmold, run the molds under hot water for a few seconds. Depending upon the temperature of your freezer, you may need a little longer. Gently remove from the molds and enjoy.