Whisk 2 tablespoons olive oil, 2 tablespoons balsamic vinegar, honey, garlic, oregano, 1 teaspoon salt and ½ teaspoon pepper in a small bowl or combine in a ziptop bag.

Place the flank steak in a large ziptop bag, pour in the marinade, press out air, and seal the bag.

Massage the marinade into the meat and refrigerate for at least 2 hours and up to 12 hours.

Combine cherry tomatoes, mozzarella pearls, remaining 1 tablespoon olive oil, remaining 1 tablespoon balsamic vinegar, ½ teaspoon salt, ¼ teaspoon pepper and chopped basil in a bowl; cover and refrigerate.

Remove the steak from the refrigerator 20 minutes before cooking.

Preheat the grill for direct high heat (about 500 °F/260 °C) and clean and oil the grates.

Remove the steak from the marinade, let excess drip off, and pat the surface dry with paper towels.

Grill the steak for 6-8 minutes per side or until an instant-read thermometer reads 130 °F/54 °C for medium-rare.

Transfer the steak to a rack-lined pan, tent loosely with foil, and rest for 5-10 minutes.

Slice the steak thinly against the grain, arrange on a platter, top with the caprese salad, garnish with basil leaves, and drizzle with balsamic glaze if using.