Preheat the oven to 350°F. Line 2 baking sheets with parchment paper.
In a bowl, combine the flour, baking powder, and salt.
Mix together butter and sugar in a separate bowl until fluffy.
Mix in the flour mixture until fine crumbs form.
Add the vanilla and combine.
* If the dough isn’t coming together, add 1 tablespoon of milk at a time as needed, until the dough forms a ball, or if the dough is impossibly sticky, sprinkle with a bit of flour.
Flatten the dough slightly, wrap it in plastic wrap, and chill for 1 hour or freeze for 15-20 minutes.
After dough has chilled, roll it out on a flat well-floured surface to about 1/4 inch thickness.
* If the dough is too sticky, sprinkle a couple tablespoons of flour over the dough and knead it a few times with your hands, roll it back into a 1/4 inch thick disc.
Use a 1 1/2-inch cookie cutter to cut dough rounds, as many as you can from the dough.
Then cut a smaller hole in the center of each cookie with a smaller cookie cutter, or using a knife,
the end of the handle on a wooden spoon, or any other small round device that you can find in your kitchen.
Press the remaining dough into a ball, roll into a 1/4 inch disc again and repeat cutting process.
Do this again until you have used as much of the dough as you can.
Transfer the rounds to the prepared baking sheets.
Bake the cookies for 10 to 12 minutes, until the bottoms are lightly browned and the cookies are set.
Cool them for a few minutes on the baking sheet, then transfer the cookies to a wire rack to cool completely.
----Make the topping---
Reduce the oven temperature to 300°F and line another baking sheet with parchment.
Spread the coconut flakes evenly on the baking sheet and toast,
stirring every 5 minutes, until the coconut is golden, about 20 minutes.
Set toasted coconut flakes aside.
In a microwave safe bowl, combine caramels and milk on high for 2 minutes.
Stir, and return to microwave for 20 seconds at a time, stirring between each, until caramel is fully melted and smooth. Stir in salt.
Spread about 1-2 teaspoons of caramel on top of each cookie.
Chill for 2-3 minutes to let the caramel set.
If the caramel becomes too firm to work with, reheat it in the microwave for a few seconds.
Stir coconut flakes into remaining caramel.
Spread the coconut-caramel topping onto the cooled cookies, up to 2 teaspoons per cookie.
Chill again while you prepare the chocolate.
Melt the chocolate chips in a double-boiler or in the microwave.
Dip the bottoms of the cookies in the chocolate and place them on parchment or a wax paper-lined baking sheet.
Transfer any remaining chocolate into a piping bag or a resealable plastic bag with one corner snipped off.
Drizzle chocolate stripes on top of the cookies.
Let the cookies sit until the chocolate hardens fully.
Note: These cookies are fairly time consuming to make, but if you take your time and have fun with them, the results will be worth it.
If any cookies make it to the end of the day, store them in an airtight container.