Melt all caramel ingredients on medium-low heat in a small saucepan, stirring periodically until fully melted and combined - about five minutes.
Distribute evenly between greased cupcake liners, about 2 tablespoons per liner.
Cupcake Instructions
Preheat oven to 350 F.
Drain can of pineapple tidbits, reserving liquid.
Remove extra moisture from the pineapple chunks by gently pressing them between paper towels.
Place about 1 tablespoon of pineapple on top of the caramel in each liner. There will be pineapple left over. You can use it decorate the cupcakes or just eat it!
In a medium-sized mixing bowl, whisk together flour, baking powder, salt, cardamom, and cinnamon. Set aside.
In another medium-sized mixing bowl or the bowl of a stand mixed, cream butter and sugar until light and fluffy.
Divide batter evenly over the pineapple in each liner, filling the liners almost all the way to the tops.
Bake for 20 minutes or until a toothpick comes out of the center of a cupcake dry. The cupcakes may have some bubbles on the top from the caramel boiling up. The tops will become the bottoms when inverted so this doesn't matter.
Let the cupcakes cool in the cupcake tins, about 15 minutes.
Once cool, remove the cupcakes from the tins, remove the liners, and carefully invert the cupcakes.
Top each cupcake with chantilly cream and a maraschino cherry.
Notes
Store at room temperature in an air-tight container for up to three days.For a more grown-up version, increase the splash of rum in the caramel sauce to a more substantial 3 tablespoons and top with a boozy Luxardo cherry instead of the kid-friendly cherries.