Preheat the grill and grate to medium-high heat. Chop the fruit, Fresh Strawberry (2 cup), Pineapple (2 cup) into even-sized pieces and add to the skewers (8-10) . Slice the Pound Cake (1) as desired.
Place the skewers and pound cake diagonally on the grill grate and cook until grill marks appear. Flip and repeat.
Set the fruit aside and add the Brown Sugar (1/2 cup) and Butter (1/2 cup) to a cast iron melting pot over medium-high heat.
Bring to a simmer, stirring often, until everything is melted and a foamy consistency is achieved.
Remove it from the heat and stir in the Heavy Cream (1/4 cup) and Vanilla Extract (1 teaspoon) until well-blended.
Scoop Vanilla Ice Cream (1 pint) into a dish, top with the grilled pound cake, cover with a skewer or two, and drizzle with the caramel sauce.