Prep & Cook: Cut the tomatoes in half, season with salt and pepper and place the tomatoes on a baking sheet covered with foil and drizzle with olive oil. Roast the tomatoes in a 425° oven for 40 minutes.
In the meantime, place olive oil in a large pot over medium heat and cook the onion until opaque. Add the garlic and red pepper flakes and stir for a minute. Add the vegetable broth, the roasted tomatoes including any drippings to the pan and stir. Add the canned tomatoes, with juices and cook for a few minutes. Add the basil, stir and simmer the soup for 35 minutes uncovered.
Using an immersion blender, blend the soup.
Serve with a loaf of bread for sopping up the soup and a nice bottle of Shiraz.