1. Coat cold grill grate with cooking spray. Preheat grill to 350° to 400° (medium-high) heat. Whisk together extra virgin olive oil and next 6 ingredients in a small bowl; whisk in 1/2 tsp. kosher salt. Arrange tomatoes on a large serving platter or in a large bowl, and drizzle with 1/4 cup vinaigrette. Sprinkle with desired amount of salt and pepper.
2. Toss shrimp with 3 Tbsp. olive oil, 1/2 tsp. freshly ground black pepper, and remaining 1/2 tsp. kosher salt. Grill shrimp, covered with grill lid, 2 minutes on each side or just until shrimp turn pink.
3. Toss grilled shrimp with remaining vinaigrette, and arrange over tomatoes. Or, if desired, toss together shrimp, remaining vinaigrette, and tomatoes.