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. Place the chocolate chips into a microwave-safe bowl. Heat in the microwave at 30 second intervals, stirring between each until chocolate is melted and smooth. Set aside.
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.
Roll apples in mixture of cherries and almonds. Place on the aluminum foil. Use a spoon to drizzle chocolate over the apples. If the chocolate is too thick, thin by mixing with a little vegetable oil. Chill until ready to serve.