Prepare the Bruschetta Topping: Preheat oven to 375 F. Peel a full head of garlic, remove all cloves, and slice into bite-size pieces. Mix garlic with 3 tbsp. olive oil, salt, and pepper. Roast on a foil-covered sheet for 20-25 minutes until golden brown.
While garlic roasts, cook 1½ cups of cherry tomatoes in 2 tbsp. olive oil on medium-high heat for 7-8 minutes. Let sit until garlic is ready.
Combine roasted garlic, cherry tomatoes, kalamata olives, 2 more tbsp. olive oil, 1 tbsp. balsamic vinegar, and a sprinkle of Italian herb seasoning in a pan. Sauté gently for 5 minutes.
If serving cold, refrigerate the topping for 45-60 minutes.
Assemble the Bruschetta: Preheat oven to 350 F. Slice bread into ½ inch pieces, dip in mixed garlic oil, and toast for 15-20 minutes.
Place a helping of burrata on each toast, spoon the tomato topping on, and garnish with a prosciutto and basil.