On a cutting board, finely chop both the macadamia nuts and peppermint bark chips. Set aside.
Preheat oven to 375.
In a stand mixer fitted with a paddle attachment, mix softened room temperature butter, powdered sugar, and vanilla extract at medium-high speed.
Add flour 1 cup at a time and mix well.
Add finely chopped macadamia nuts and peppermint bark chips, mix well.
Roll out cookie dough ¼" thick on lightly floured surface with a rolling pin, and cut into pineapple shapes. Place on parchment-lined baking sheet.
In a small glass bowl, melt about 1 cup of the peppermint bark (chips) in the microwave on high for 30 seconds, keep melting in 30-second increments until just melted and stir.
Bake for 20-22 minutes, or until edges are slightly golden brown. Cool cookies completely on wire racks.
Place melted peppermint chocolate in a strong gallon zip-top bag, snip a tiny corner of the bag the tip, and decorate with drizzles of melted peppermint bark in a criss-cross pattern on the pineapple cookies.
Let the melted chocolate set for a couple of hours before stacking the cookies so the "icing" dries in an airtight container.
Enjoy, and Mele Kalikimaka.
If you want to make the cookie dough ahead, you can wrap it really well in plastic wrap, and keep chilled in the fridge or freezer until ready to bake.