In a large bowl, mix together graham cracker crumbs, butter, and sugar. Press mixture into the bottom and up the sides of a 9x13" baking pan. Place the crust in the fridge while you make the next layer.
In another bowl, beat cream cheese, pineapple and powdered sugar together. Stir in the vanilla extract. Remove the prepared crust from the fridge and spread cream cheese mixture onto crust.
Rinse out the bowl and then use it to mix together the milk and pudding mix. Whisk until it starts to thicken up (it will take about 2 minutes). Fold in 1 cup of the Cool Whip, then spread the pudding mixture on top of the cream cheese layer.
Spread the remaining Cool Whip on top as the final layer.
Sprinkle with toasted coconut and place dessert in the fridge to set up (let it stay refrigerated for at least 2-3 hours).
If desired, top each piece with a maraschino cherry when serving.
Notes
If you want to toast your coconut, here’s how:Preheat oven to 325ºF. Place shredded coconut in a single layer on a large baking sheet that has been lined with a baking mat or parchment paper.Put the baking sheet on the middle rack and bake for 3 minutes. After 3 minutes, open the oven and gently stir the coconut with a spatula. Bake until the coconut is golden brown, about 3–4 more minutes (watch carefully because one it starts to brown, it can burn very quickly!). Remove from oven and cool completely, then use as a topping for your dessert.You can make this dish a day in advance and it will be perfect to eat the next day.