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.

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.

Toss grilled shrimp with remaining vinaigrette, and arrange over tomatoes. Or, if desired, toss together shrimp, remaining vinaigrette, and tomatoes.