Preheat oven to 350 degrees Fahrenheit.
Slice the challah loaf.
1 loaf challah bread
In a large bowl whisk together the eggs, milk, cinnamon, and 1 teaspoon vanilla.
4 large eggs, 1 cup whole milk, 2 teaspoons vanilla extract, 1/2 teaspoon cinnamon
Arrange the slices of bread in a deep oven safe baking dish. We love using a dutch oven or a similar circular dish with high sides, approximately 12-14 inch round!
Pour the egg mixture over the top of the challah slices. Try to distribute it evenly across the slices. Cover and let soak for at least 30 minutes or overnight.
Remove cover and bake for 35-40 minutes or until most of the liquid has been absorbed.
Separately, in a pan melt butter on medium-high heat.
8 Tablespoons unsalted butter
Add the brown sugar, heavy cream, salt, and the remaining vanilla. Whisk it together until it is thoroughly combined. Reduce the heat to medium and let cook for 2-3 minutes, it will look like a caramel sauce.
3/4 cup packed light brown sugar, 1/4 cup heavy cream, 1/2 teaspoon sea salt
Next, slice your bananas and add into the caramel sauce. Reduce heat to low and let simmer for 1-2 minutes or just until bananas begin to slightly soften. Scoop the caramel sauce and bananas on top of the challah slices.
2 medium bananas