In a medium sealable jar, mix together bourbon, water, sugar, orange peel, vanilla extract, and cinnamon. Add in cherries. Seal and allow to soak at least overnight, but preferably for a full 24-48 hours.
to make the bread
Preheat oven to 350°F. Line a large loaf pan with parchment paper. Set aside.
In a large bowl, cream brown sugar and butter. Add in bananas, eggs, milk, and vanilla.
Whisk in flour, baking soda, and salt.
In a separate bowl, drain the bourbon-soaked cherries and toss in 2 tablespoons of flour. Gently fold into batter.
Pour into loaf pan and top with banana sliced in half, if using. Bake for roughly 1 hour, until a knife inserted in the center of the loaf comes out clean. Cool on a wire rack before serving!