Combine first 3 ingredients in a small saucepan; cook over medium heat 4 minutes or until mixture is thick. Add bourbon; cook until mixture is reduced to 1/4 cup (about 5 minutes). Remove from heat. Add sliced bananas, and toss gently. Spoon banana mixture into a bowl; set aside.
Combine milk and next 5 ingredients (through eggs) in a large bowl, stirring well with a whisk. Add bread; stir to combine. Divide bread mixture evenly among 6 (8-ounce) ramekins coated with cooking spray. Divide banana mixture evenly over bread mixture. Place ramekins on a small baking sheet. Cover and chill 30 minutes.
Preheat oven to 375°.
Uncover and bake at 375° for 25 minutes or until set. Drizzle caramel topping evenly over bread puddings.