In a small bowl or measuring cup, whisk together ¼ cup olive oil, red wine vinegar, garlic, parsley and basil.
In a non-reactive dish or ziploc bag add flank stead and cover with marinade. Let meat marinate 4-6 hours. Remove meat 30 minutes prior to grilling.
Preheat oven to 400ºF.
Preheat grill. Set burners to high heat.
In a small bowl whisk together salt, pepper, remaining 2 tablespoon olive oil, balsamic vinegar and Italian seasoning. Mix in cherry tomatoes and toss to coat.
Pour tomatoes onto a baking sheet and roast in the hot oven for 20 minutes.
Meanwhile, remove meat from the marinade and pat dry with paper towels.
Place steaks on hot grill and cook until browned, about 6 to 7 minutes. Turn steaks over and continue grilling 6 to 7 minutes for medium-rare doneness. Flank steak is best served medium-rare, as it can toughen if over-cooked.
Remove from the grill and place steaks on serving platter. Cover steak with foil, and let steaks rest 5 minutes before serving.
Prior to serving, carve steak into long strips. Top with roasted tomatoes and serve hot.
Notes
TO STORE: Store any leftover roast in an airtight container and refrigerate for up to 4 days.TO FREEZE: You could also freeze leftovers, but I suggest not to do this as the texture does change when frozen and thawed.