Make the roasted garlic and roasted grape tomatoes with basil.
Heat the olive oil in a large Dutch oven over medium heat, then add the onion, carrots, and celery. Cook, stirring frequently for 4-5 minutes.
Squeeze the roasted garlic into the mixture, then add the roasted tomatoes, two cans of tomatoes, basil, oregano, bay leaf, vinegar, and broth. Season with sea salt and freshly cracked pepper, to taste.
Let the soup simmer for 2 hours, stirring occasionally.
Remove the bay leaf, then blend the soup using an immersion blender until thoroughly mixed. Taste the soup and add sugar if you want your soup slightly sweet, more sea salt, or freshly cracked pepper if needed.
You can also add ½ cup of half & half or heavy cream for a richer, creamier soup. Side Note: For a thinner soup, pour through a strainer.