Insert wooden sticks 3/4 of the way into the stem end of each apple. Place apples on a cookie sheet covered with lightly greased aluminum foil.
Combine caramels and water in a saucepan over low heat. Cook, stirring often, until caramel melts and is smooth. Stir in the vanilla. Dip each apple into the caramel and gently run apples around insides of saucepan to scrape off some of the caramel. Scrape excess caramel from the apple bottoms using the side of the saucepan.
Combine the miniature marshmallows and graham crackers on a dinner plate. Roll the apples in the mixture to coat. Place on the aluminum foil and chill.
Put the chocolate chips in a microwave-safe bowl. Cook in the microwave for 30 second intervals, stirring between each, until melted and smooth. Drizzle over the apples and return them to the refrigerator until ready to serve.