Preheat the oven to 350° and line a large baking sheet with parchment paper and set aside. In a large bowl add the sugar and butter and cream the butter with a hand mixer, until light and fluffy.
Add the baking soda, salt and flour and beat slowly. Add the milk and vanilla and continue beating until everything combines and a dough forms.
Take two trays and line with parchment paper. Divide the dough in half and place each half on each tray. Slightly press out into a disc shape and then cover with plastic wrap and place in the refrigerator for 45 minutes.
Lightly flour a flat clean space. Take one of the chilled doughs and sprinkle more flour on top, roll out the dough with a rolling pin until it’s about 1/8 inch thick. Use a cookie cutter to cut out as many cookies as you can. Place them on the lined baking sheet.
Use a cookie cutter about the size of a quarter to cut a circle out the middle of each cookie. Remove the middle. Repeat with the other chilled dough. Bake the cookies in the oven for 12-15 minutes, or until a light golden brown color.
Once they are baked let them cool completely. In a large pan add the shredded coconut and cook on a medium to high heat while stirring constantly until it becomes a dark golden brown color. In a medium pot add the milk and caramels, melt over a medium to low heat while stirring constantly.
Add about 1/3 of a cup of the melted caramel to the toasted coconut, stir to combine. Take a cooled cookie and dip the top of it in the caramel, use two forks to lightly dip in the caramel and lift back up. Place back down on the baking sheet with the caramel side facing up.
Take the toasted coconut and press it into the wet caramel on the cookie all around. Repeat until all the cookies are done. In a medium sized microwave safe bowl add the dark chocolate and microwave until melted, stirring every 30 seconds.
Dip the bottoms of the cookies into the chocolate using the two fork trick and place back on the baking sheet, add the rest of the chocolate into a small zip lock bag and cut a tiny bit of the corner off and drizzle on top of the cookies.
Let the chocolate harden (about 10 minutes) then serve and enjoy!!