Place a medium mixing bowl and beaters in the fridge or freezer while you prepare the crust.
Add graham crackers to a food processor and pulse until fine crumbs form. Transfer the crumbs to a medium bowl and mix with the melted butter and sugar, until evenly combined. Press the mixture into the bottom and up the sides of a 9-inch pie plate. Chill the crust while you prepare the filling.
Remove the bowl and beater(s) from the refrigerator and add cold cream and whip until soft peaks begin to form. Then add powdered sugar and continue beating until stiff peaks form. Set aside.
Drain the can of crushed pineapple by pressing it through a sieve. Set this aside.
In a large mixing bowl beat the cream cheese until smooth. Then beat in the sugar and rum extract.
Mix in the well-drained pineapple and coconut. Then gently fold in the whipped cream.
Transfer the mixture to the prepared pie crust and chill for at least 3 hours in the refrigerator.
After chilling, pipe on fresh whipped cream and top with toasted coconut, maraschino cherry, and pineapple slices, if desired.