How to Make It
Preheat oven to 425°F. Place bananas (in peel) on a baking sheet, and bake in preheated oven until peel is very dark and just starting to split open, 20 to 25 minutes. Let bananas cool completely, about 20 minutes. Remove and discard peels.
Place roasted bananas, ice cream, milk, caramel topping, and vanilla in a blender. Process until completely smooth, about 45 seconds. Pour into 4 glasses, and top with whipped cream, a drizzle of caramel topping, and banana slices.