Mix the ginger snap crumbs and melted butter. Press firmly into a 9-inch pie plate. Bake at 350°F for 8 minutes to set the crust and bring out the ginger aroma. Let it cool completely.
While the oven is on, spread the shredded coconut on a baking sheet. Toast for 3–5 minutes until golden brown and fragrant. Set aside to cool.
In a large bowl, beat the softened cream cheese with the confectioners' sugar, coconut extract, and dark rum until smooth and airy.
In a separate chilled bowl, whip the heavy cream until stiff peaks form. Gently fold the whipped cream into the cream cheese mixture. Finally, fold in the well-drained crushed pineapple.
Pour the tropical filling into the cooled ginger snap crust. Smooth the top with a spatula.
Refrigerate for at least 4 hours, or ideally overnight. This allows the flavors to marry and the filling to become firm enough to slice cleanly.
Just before serving, top with the toasted coconut. Garnish with cherries and pineapple wedges to give it that classic resort-style look.