In a large oven and broiler safe skillet, heat 1 ½ tbsp of extra-virgin olive oil over medium heat. Add the garlic and cook until almost brown, about 1 minute. Increase the heat to high and add the grape tomatoes, Italian seasoning, salt and pepper. Cook, stirring occasionally, for about 5 minutes.
Add orzo and chicken broth. Bring to a simmer. Remove skillet from heat and transfer to pre-heated oven. Bake until most of the liquid has absorbed, 10 to 12 minutes.
Meanwhile, toss the shrimp in the remaining ½ tbsp. of olive oil. Season with salt and pepper. Remove skillet from oven and evenly place shrimp on top of the orzo. Turn oven to broil. Broil on high until shrimp is opaque throughout, about 4 minutes.