In a large mixing bowl, beat the cream cheese until it's fluffy, about 1 minute.
Add the pudding mix, pineapple juice, heavy cream, and vanilla to the mixing bowl and beat until combined and thickened.
Add the pineapple and shredded coconut to the pie filling. Stir until evenly combined.
Pour the pie filling into your prepared pie crust. Spread into an even layer.
Cover the pie with plastic wrap and refrigerate for 4 hours, or until the pie is set. Keep the pie refrigerated until ready to serve. The garnishes should be added at the last minute.
To garnish: Uncover the pie. Sprinkle toasted coconut over the top of the pie going almost all the way to the edges. Add whipped cream in dollops around the outer edge of the pie and one in the center. Place cherries evenly around the edge of the pie on top of the whipped cream and then place a cherry on the center dollop.
If you can't find coconut cream pudding mix, use vanilla pudding with coconut cream (or coconut milk) instead of heavy cream and omit the vanilla extract. If you want a more authentic Pina Colada flavor, you can also add 1/4 teaspoon of rum extract to the pie filling.