Preheat oven to 325 degrees F. Butter the sides and bottom of a large bread loaf pan. Line long sides of pan with a parchment paper sling. Set aside.
Add light brown sugar, granulated sugar, and unsalted butter to stand mixer. Using the paddle attachment, beat until light and fluffy, about 2 minutes. Add the eggs one at a time, beating well after each addition. Remove the bowl from the mixer.
Add the peeled bananas to a small bowl. Mash with the back of a fork. Stir in the whole milk and ground cinnamon. Add the banana mixture to the sugar mixture Fold in with large spatula until well combined.
Add the all-purpose flour, baking powder, baking soda and fine sea salt to a medium mixing bowl. Whisk to combine. Add the flour mixture to the banana mixture. Fold in with large spatula.
Add the roughly chopped chocolate, roughly chopped pecans and roughly chopped fresh cherries to the banana bread batter, reserving a few of each to adorn the top. Fold in using a large spatula.
Transfer the banana bread batter into prepared bread loaf pan and smooth evenly into the corners with a small offset spatula.
Sprinkle reserved crumb topping over surface of bread batter.
Peel and cut two 1/8-inch thick lengthwise slices of banana. Arrange slices on top of bread batter. Sprinkle reserved chocolate, pecans, and cherries over bread batter.
Bake 70 minutes in preheated oven, or until a toothpick inserted in the center comes out clean.
Remove loaf pan from oven and cool on wire rack. Remove banana bread from loaf pan using parchment paper sling. Run a paring knife around edges of bread to loosen, if necessary.
Remove bread from pan, and cool completely before slicing.