In a mixing bowl, beat the softened cream cheese with an electric mixer until smooth and creamy, about 2 minutes.

Add the powdered sugar and vanilla extract, mixing until well combined.

Gently fold in the drained crushed pineapple using a spatula, ensuring the mixture is evenly distributed.

In a separate bowl, whip the chilled heavy cream until stiff peaks form. This will give the filling a light and airy texture.

Carefully fold the whipped cream into the pineapple mixture until fully incorporated.

In a bowl, combine the graham cracker crumbs and melted butter. Mix until the crumbs are evenly coated.

Spread half of the graham cracker mixture evenly in the bottom of a 9x13 inch baking dish to form the base.

Dip each graham cracker sheet quickly in milk (do not soak) and layer them over the graham cracker base.

Spread half of the pineapple filling over the graham cracker layer.

Repeat the process: layer more dipped graham crackers, followed by the remaining pineapple filling.

Finish with a final layer of dipped graham crackers on top.

Cover the dish with plastic wrap and refrigerate for at least 4 hours, or overnight if possible. This allows the flavors to meld and the graham crackers to soften.

Before serving, top with whipped cream and sprinkle with toasted coconut flakes if desired.

Slice into squares and enjoy your refreshing Pineapple Icebox Cake!