Preheat the Oven: Start by preheating your oven to 350°F (175°C). Prepare a 12-cup muffin tin by lining it with paper liners, which will make removing the cheesecakes easier.
Prepare the Crust: In a medium mixing bowl, combine 1.5 cups of graham cracker crumbs with 1/4 cup of melted butter. Mix until the crumbs are fully coated in butter. Press this mixture firmly into the bottom of each muffin cup to create a sturdy base for your cheesecakes.
Make the Cheesecake Filling: In a large bowl, beat 2 packages (8 oz each) of softened cream cheese together with 1/2 cup of granulated sugar until smooth and creamy, ensuring there are no lumps. Add 2 large eggs one at a time, mixing well after each addition. Finally, stir in 1 tsp of vanilla extract until fully incorporated.
Assemble: Spoon the cheesecake filling into the muffin cups over the crust, filling each cup about 2/3 full. Top each cheesecake with drained pineapple chunks, distributing evenly among the cups.
Bake: Place the muffin tin in the preheated oven and bake for about 20-25 minutes. The edges should be set, while the centers will still be slightly jiggly. Remove from the oven and allow to cool completely in the pan.
Chill and Serve: After cooling, refrigerate the cheesecakes for at least 4 hours, allowing them to firm up. Before serving, drizzle with 1/4 cup of caramel sauce to elevate their flavor. For an extra touch, consider garnishing with a cherry or a sprig of mint.