Preheat oven to 400℉. Line two baking sheets with parchment paper.
Spread the quartered tomatoes evenly between the two pans. Drizzle each pan with 1 tablespoon olive oil. Sprinkle with salt and pepper.
Prepare garlic by slicing top off and peeling away any loose sheath. Wrap in aluminum foil with opening at top - drizzle 1 tablespoon of olive oil in the opening, and place in middle of one of the pans. *See pictures in post.
Place the tomatoes and garlic in the preheated oven for 55 minutes - 1 hour, or until the tomatoes begin to caramelize around the edges. Remove from oven and let cool 5-10 minutes. Squeeze garlic head to remove roasted garlic, using caution as bulb will be HOT!
While tomatoes and garlic are roasting, heat remaining tablespoon of oil in large pot over medium heat. Add onions and saute 4-5 minutes or until soft and translucent.
Add dried herbs and sauté until aromatic, about 10 seconds.
Add balsamic vinegar and brown sugar to pot and sauté about 20-30 seconds or until vinegar is absorbed and sugar is blended being careful not to burn.
Add vegetable broth, bring to a simmer and cook 10 minutes. Remove from heat.
Remove from oven and let cool 5-10 minutes.
Using caution as the bulb will be hot - squeeze garlic head to remove roasted garlic from the sheath.
Add tomatoes and garlic to pot. Using an immersion blender, blend until desired texture. Or, if using a high-speed blender, add tomatoes, garlic and broth directly to the blender working in batches. Return to pot.
Place back on stove over medium heat. Add cream and fresh basil, adjusting seasonings as desired. Heat through
Ladle soup to bowls and top with Parmesan cheese or additional basil if desired. Enjoy!