Preheat oven to 400 degrees Fahrenheit
Prepare 2 baking sheets by lining with parchment paper.
Spread tomaotes evenly between pans. Drizzle each pan with 1 tablespoon olive oil. Spinkle with 1/4 tsp salt and pepper. *See note
Prepare garlic by slicing top off and peeling away any loose sheath. Wrap in aluminum foil with opening at top - drizzle with 1 tablespoon olive oil, and place in middle of one of the pans. *See pictures
Place in preheated oven for 55 minutes - 1 hour. 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 cook 30 seconds.
Add balsamic vinegar to pot and cook about 1 minute or until vinegar is absorbed.
Add vegetable broth, bring to a simmer and cook 10 minutes. Remove from heat.
Add tomatoes and garlic to pot. Using an immersion blender, blend until desired texture.
Place back on stove over medium heat. Add cream, fresh basil, remaining salt and pepper and heat through.
Enjoy!