Preheat Oven: Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper.
Cream Butter and Sugar: In a large bowl, cream the softened butter and sugar together until light and fluffy. Add the vanilla extract and mix well.
Mix Dry Ingredients: In a separate bowl, whisk together the flour and salt. Gradually add the dry ingredients to the butter mixture, mixing until a dough forms.
Shape Cookies: Roll out the dough on a lightly floured surface to about 1/4-inch thickness. Use a round cookie cutter (about 2 inches in diameter) to cut out circles. Use a smaller cutter (or the end of a piping tip) to cut out the centers to create a doughnut shape.
Bake: Place the cookies on the prepared baking sheet and bake in the preheated oven for 10-12 minutes, or until the edges are lightly golden. Allow them to cool on the baking sheet for a few minutes before transferring to a wire rack to cool completely.
Prepare the Topping:
Toast the Coconut: Spread the shredded coconut evenly on a baking sheet and bake at 350°F (175°C) for 5-7 minutes, stirring occasionally, until golden. Watch closely to prevent burning. Remove and let cool.
Melt the Caramels: In a microwave-safe bowl, combine the caramels and milk (or heavy cream). Microwave in 20-second intervals, stirring in between, until the caramel is smooth and melted.
Combine Caramel and Coconut: Stir the toasted coconut into the melted caramel until well combined.
Assemble the Cookies:
Top the Cookies: Spread a layer of the caramel-coconut mixture on top of each cookie. Allow to set for a few minutes.
Melt the Chocolate: In a microwave-safe bowl, melt the chocolate chips in 20-second intervals, stirring in between, until smooth.
Dip and Drizzle: Dip the bottom of each cookie into the melted chocolate and place on parchment paper. Use a fork or piping bag to drizzle more chocolate over the top of each cookie.
Cool and Set: Let the cookies cool completely at room temperature, or place them in the refrigerator to set the chocolate faster.