In a medium bowl, combine the graham cracker crumbs, brown sugar, and melted butter, stirring until everything is evenly mixed.
Evenly distribute the graham cracker mixture into 6 mason jars. Use the back of a spoon (or the bottom of a small glass/measuring cup) to press it down firmly and evenly across the bottom of each jar.
Using a medium bowl and an electric mixer on high speed, beat the heavy whipping cream for 4–5 minutes until it holds stiff peaks (the peaks should stand straight up when you lift the beaters). Set it aside for now.
In another bowl, use your mixer to beat the cream cheese, sugar, sour cream, and coconut extract until silky-smooth with no lumps remaining—about 2–3 minutes on medium speed.
Add 1 cup pineapple tidbits and ½ cup sweetened coconut flakes to the creamy cheesecake mixture.Fold them in carefully with a spatula so you keep that light, fluffy texture—no heavy stirring!
Spoon the pina colada cheesecake mixture evenly into the 6 jars, layering it gently over the prepared crust in each.Place the jars in the refrigerator and chill for at least 4 hours (or longer for firmer results).
When you’re ready to serve, add ¼ cup coconut flakes to a dry skillet over medium-low heat.
Stir constantly for 3–5 minutes until it turns a beautiful golden brown—watch closely so it doesn’t burn!Remove from the heat right away and pour into a bowl to cool completely.
Once the toasted coconut has cooled, take the cheesecake jars out of the fridge.
Top each one with extra pineapple tidbits, a generous sprinkle of toasted coconut, and a maraschino cherry. Serve and enjoy!