Beat cream cheese and condensed milk at medium speed with an electric mixer 2 minutes.
Beat dry pudding mix and milk in a large bowl at medium speed with an electric mixer 2 minutes; add vanilla, and beat 30 seconds. Add cream cheese mixture, and beat 1 minute. Fold in whipped topping.
Spoon one-third of pudding mixture into a 4-quart bowl; drizzle with about 2 1/2 tablespoons caramel syrup. Layer with one-third each of bananas and vanilla wafers. Repeat layers twice with pudding mixture, caramel syrup, bananas, and ending with vanilla wafers, flat sides down, placed in a single ring around edge of bowl. Cover and chill at least 6 hours.