Preheat the oven to 350°F (175°C). Line a baking sheet with parchment paper.
Beat softened butter and sugar in a mixing bowl until light and creamy. Add vanilla extract. Gradually mix in flour and salt until the dough comes together.
Roll the dough into a 1/4-inch thick sheet between two pieces of parchment paper. Use a 2-inch round cookie cutter to cut out cookies, and cut out small center holes with a smaller cutter.
Place the cookies on the prepared baking sheet and bake for 10–12 minutes or until lightly golden around the edges. Let cookies cool completely on a wire rack.
Spread the shredded coconut on a baking sheet and toast in the oven for 8–10 minutes, stirring halfway through, until lightly golden.
Melt the caramels and heavy cream in a microwave-safe bowl in 30-second intervals, stirring between each, until smooth.
Spoon a small amount of the melted caramel onto each cookie and spread it thinly to create a sticky base for the topping.
Stir the toasted coconut into the remaining caramel mixture until well combined. Scoop a small portion of the mixture onto each cookie.
Use your hands or fingers to shape and press the coconut-caramel topping firmly onto each cookie, covering the top and edges. Dip your fingers in water as needed to prevent the mixture from sticking to your hands.
Melt the chocolate chips in a microwave-safe bowl in 20-second intervals, stirring until smooth.
Dip the bottom of each cookie into the melted chocolate and place them on parchment paper to set. Use a fork or piping bag to drizzle melted chocolate over the top of the cookies.
Let the cookies cool completely until the chocolate hardens. Serve and enjoy!