Preheat oven to 400 degrees
To prepare, line a baking sheet with parchment paper and add quartered tomatoes and onions. Include 2 whole heads of garlic, and for an extra flavor boost, add peeled garlic cloves. Drizzle the ingredients generously with olive oil, and season with a blend of salt, pepper, 1 tsp of Italian seasoning and 1/2 tsp all purpose seasoning. Mix everything together until the veggies are well coated.
Roast the veggies in the oven for approximately 40 minutes or until the vegetables are soft and caramelized. Let the roasted vegetables cool for about 10-15 minutes before transferring them to a blender. If you have an immersion blender, you can skip this step.
Add the roasted vegetables, red pepper flakes, thyme, and fresh basil to a blender and blend until smooth. Strain the mixture into a saucepan over medium heat. Stir in Calabrian chilies, onion powder, garlic powder, 1 tsp of Italian seasoning, all-purpose seasoning, and a touch of sugar to balance the flavors. Simmer over medium heat for about 10 minutes.
Add in 1 cup of broth or water if desired, to thin out the soup.
Pour in heavy cream to make it creamy. Allow to simmer for an additional 7 minutes and let all the ingredients meld together. Taste the soup and adjust the seasonings according to your preference
Ladle the soup into a bowl. Top with extra virgin olive oil and fresh basil. Enjoy!
