Preheat your oven to 400℉.
Place the halved tomatoes cut side up with the onions on a parchment baking sheet. Drizzle with ¼ cup of the olive oil and sprinkle salt and pepper over the top. Roast for 40-50 minutes, until tomatoes are slumped looking, turning golden brown. Remove from the oven. Complete this before moving on to the next step.
6 roma tomatoes, 1 yellow onion, ⅓ cup olive oil, ½ teaspoon kosher salt, ½ teaspoon black pepper
In a heavy bottomed pot or dutch oven over medium heat, sauté the minced garlic, fresh thyme, and saffron in the remaining olive oil and the butter for just a minute or two, stirring frequently. Garlic burns easily, so don't overcook it!
2 tablespoon butter, 5 cloves garlic, 1 teaspoon fresh thyme leaves, 1 pinch saffron strands, ⅓ cup olive oil
Add the roasted tomatoes and onions with the accumulated juices to the pot along with the canned tomatoes and chicken broth. Let the soup simmer for 25-30 minutes, but add the basil 5 minutes before finishing the simmer time.
1 (28 oz) can San Marzano tomatoes, 6 cups chicken broth, ½ cup fresh basil leaves
TURN OFF THE HEAT BEFORE IMMERSION BLENDING! After you turn the heat off, use an immersion blender to carefully blend the tomato soup smooth. If you want a super-smooth soup, strain it through a fine sieve. Taste and season with salt and pepper as needed.
kosher salt and freshly cracked black pepper
Serve the soup in bowls with a drizzle of heavy cream for richness, a few fresh basil leaves for garnish, and the grilled cheese sandwich on the side. I like to cut mine in half and use the other half as croutons.
heavy cream