In a large mixing bowl, combine the mashed bananas, softened butter, Greek yogurt, brown sugar, egg, and vanilla. Use a spatula or whisk to mix until everything is well incorporated.
In another bowl, whisk together the flour, baking soda, baking powder, and salt.
Gradually add the dry ingredients to the wet mixture. Stir gently until just combined; be careful not to overmix.
If using frozen cherries, ensure they are thawed and pat them dry with a paper towel. In a small bowl, toss the cherries with the 2 tablespoons of flour to coat them lightly.
Gently fold the floured cherries and chocolate chips into the batter until evenly distributed.
Pour the batter into your prepared loaf pan, smoothing the top with a spatula.
Bake in the preheated oven for 55-65 minutes, or until a toothpick inserted into the center comes out clean. Keep an eye on it towards the end of the baking time to avoid overbaking.
Once baked, remove the bread from the oven and let it cool in the pan for about 10 minutes. Then, transfer it to a wire rack to cool completely before slicing.