Preheat oven to 325°F (163°C) and line a 12-cup muffin pan with cupcake liners.

Add ½ teaspoon caramel sauce to each cupcake liner. Place one pineapple chunk on top of caramel and sprinkle a pinch of granulated sugar over each pineapple.

In a bowl, mix graham cracker crumbs and melted butter until combined. Press about 1 tablespoon of crust mixture firmly into each liner on top of the pineapple.

Beat cream cheese and sugar together until smooth and creamy (2-3 minutes). Add eggs one at a time, mixing gently until just combined. Stir in vanilla extract.

Divide cheesecake batter evenly among muffin cups, filling nearly to the top. Bake for 18-22 minutes until centers are set but slightly jiggly. Cool in the pan for 15-20 minutes, then refrigerate for at least 2 hours before serving.

Carefully remove cupcake liners and place cheesecakes upside down on serving plates. Garnish with a cherry, whipped cream, or toasted coconut if desired.