In a medium bowl, combine 2 ½ cups of graham cracker crumbs, 4 tablespoons of sugar, and 6 tablespoons of melted unsalted butter. Mix until well incorporated, resembling wet sand. Press this mixture firmly into the bottom of a greased 9-inch springform pan, creating an even layer. Once formed, freeze the crust for 10-15 minutes to allow it to firm up before adding the filling.

While the crust chills, prepare the cheesecake filling. In a large mixing bowl, beat 16 oz of softened cream cheese and 1 cup of powdered sugar together until the mixture is smooth and creamy. In a separate bowl, whip 2 cups of heavy cream to soft peaks. Gently fold the whipped cream into the cream cheese mixture, being careful not to deflate the whipped cream, until combined into a light, airy filling.

Stir in 1 cup of well-drained crushed pineapple, ½ cup of sweetened shredded coconut, and 1 teaspoon of rum extract into the cream cheese mixture. Mix gently until all the ingredients are well incorporated.

Spread the cheesecake filling over the chilled crust in the springform pan. Use a spatula to smooth the top, creating an even surface. Cover the pan with plastic wrap and refrigerate it for at least 3-4 hours, or until the cheesecake is fully set.

Once the setting time has passed, carefully run a knife around the edge of the springform pan to release the cheesecake. Carefully remove the sides of the pan and place the cheesecake on a serving platter. Garnish with dollops of whipped cream, maraschino cherries, and fresh pineapple pieces before slicing and enjoying.